Hetaryl-substituted heterocycles

ABSTRACT

The invention relates to novel compounds of formula (I) in which A, B, W, G and Het have the same designation cited in the description. The invention also relates to several methods for the production of said new compounds and the use thereof as pesticides and herbicides.

[0001] The present invention relates to novel hetaryl-substitutedheterocycles, to a plurality of processes for their preparation and totheir use as pesticides and herbicides.

[0002] 4-Thiazolyl-3-hydroxy-3-pyrroline-2,5-diones are known asglycolic acid oxidase inhibitors; U.S. Pat. No. 4,296,237; U.S. Pat. No.4,377,588; EP-A-025 232; Rooney C. S. et al., J. Med. Chem. 26 700-714(1983); Guzel Y. et al. THEOCHEM 366 131-137 (1996).

[0003] The present invention provides novel compounds of the formula (I)

[0004] in which

[0005] W represents N—D⁽¹⁾, oxygen⁽²⁾ or sulphur⁽³⁾,

[0006] Het represents in each case optionally substituted thiazolyl,oxazolyl or pyrazolyl,

[0007] A represents hydrogen, in each case optionallyhalogen-substituted alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl,alkylthioalkyl, saturated or unsaturated optionally substitutedcycloalkyl in which optionally at least one ring atom is replaced by aheteroatom, or in each case optionally halogen-, alkyl-, halogenoalkyl,alkoxy-, halogenoalkoxy-, cyano- or nitro-substituted aryl, arylalkyl orhetaryl,

[0008] B represents hydrogen, alkyl or alkoxyalkyl, or

[0009] A and B together with the carbon atom to which they are attachedrepresent a saturated or unsaturated unsubstituted or substituted cyclewhich optionally contains at least one heteroatom,

[0010] D represents hydrogen or represents an optionally substitutedradical from the group consisting of alkyl, alkenyl, alkinyl,alkoxyalkyl, polyalkoxyalkyl, alkylthioalkyl, saturated or unsaturatedcycloalkyl in which optionally one or more ring members are replaced byheteroatoms, arylalkyl, aryl, hetarylalkyl or hetaryl or

[0011] A and D together with the atoms to which they are attachedrepresent a saturated or unsaturated cycle which is unsubstituted orsubstituted in the A,D moiety and optionally contains at least oneheteroatom,

[0012] G represents hydrogen (a) or represents one of the groups

[0013] in which

[0014] E represents a metal ion equivalent or an ammonium ion,

[0015] L represents oxygen or sulphur,

[0016] M represents oxygen or sulphur,

[0017] R¹ represents in each case optionally halogen-substituted alkyl,alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl or optionallyhalogen-, alkyl- or alkoxy-substituted cycloalkyl which may beinterrupted by at least one heteroatom, in each case optionallysubstituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl orhetaryloxyalkyl,

[0018] R² represents in each case optionally halogen-substituted alkyl,alkenyl, alkoxyalkyl, polyalkoxyalkyl or represents in each caseoptionally substituted cycloalkyl, phenyl or benzyl,

[0019] R³ represents alkyl, halogenoalkyl or represents in each caseoptionally substituted phenyl or benzyl,

[0020] R⁴ and R⁵ independently of one another each represent in eachcase optionally halogen-substituted alkyl, alkoxy, alkylamino,dialkylamino, alkylthio, alkenylthio, cycloalkylthio and represent ineach case optionally substituted phenyl, benzyl, phenoxy or phenylthio,

[0021] R⁶ and R⁷ independently of one another each represent hydrogen,in each case optionally halogen-substituted alkyl, cycloalkyl, alkenyl,alkoxy, alkoxyalkyl, represent optionally substituted phenyl, representoptionally substituted benzyl, or together with the N atom to which theyare attached represent a cycle which is optionally interrupted by oxygenor sulphur.

[0022] Depending inter alia on the nature of the substituents, thecompounds of the formula (I) can be present as geometrical and/oroptical isomers or isomer mixtures in varying composition which may, ifdesired, be separated in a customary manner. The present inventionprovides both the pure isomers and the isomer mixtures, theirpreparation and use, and compositions comprising them. However,hereinbelow, compounds of the formula (I) are always referred to for thesake of simplicity, although what is meant are both the pure compoundsand, if appropriate, also mixtures with varying proportions of isomericcompounds.

[0023] Including W═N—D⁽¹⁾, oxygen⁽²⁾ or sulphur⁽³⁾, the followingprincipal structures (I-1) to (I-3) result:

[0024] in which

[0025] A, B, D and G are each as defined above and

[0026] Het represents thiazolyl or oxazolyl.

[0027] Including the various meanings of Het, the following principalstructures result:

[0028] (I-1-A) to (I-3-B) if W represents N—D⁽¹⁾, oxygen⁽²⁾ or sulphur⁽³⁾

[0029] in which

[0030] A, B, D and G are each as defined above and

[0031] X represents hydrogen, halogen, alkyl, halogenoalkyl, alkoxy,halogenoalkoxy, alkenyloxy, haloalkenyloxy, nitro, cyano or optionallysubstituted phenyl,

[0032] Y represents halogen, alkyl, halogenoalkyl, alkoxy,halogenoalkoxy, alkenyloxy, alkylthio, alkylsulphinyl, alkylsulphoxinyl,alkylsulphonyl or represents in each case optionally substituted phenyl,benzyl, phenoxy or phenylthio.

[0033] Including the various meanings (a), (b), (c), (d), (e), (f) and(g) of the group G, the following principal structures (I-1-A-a) to(I-1-A-g) result if W represents N—D⁽¹⁾

[0034] A, B, D, E, L, M, X, Y, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷are each asdefined above.

[0035] Including the various meanings (a), (b), (c), (d), (e), (f) and(g) of the group G, the following principal structures (I-1-B-a) to(I-1-B-g) result if W represents N—D⁽¹⁾

[0036] A, B, D, E, L, M, X, Y, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ are each asdefined above.

[0037] Including the various meanings (a), (b), (c), (d), (e), (f) and(g) of the group G, the following principal structures (1-2-A-a) to(I-2-A-g) result if W represents oxygen⁽²⁾

[0038] A, B. E, L, M, X, Y, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ are each asdefined above.

[0039] Including the various meanings (a), (b), (c). (d), (e), (f) and(g) of the group G, the following principal structures (I-2-B-a) to(I-2-B-g) result if W represents oxygen⁽²⁾

[0040] A, B, E, L, M, X, Y, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ are each asdefined above.

[0041] Including the various meanings (a), (b), (c), (d), (e), (f) and(g) of the group G, the following principal structures (I-3-A-a) to(I-3-A-g) result if W represents sulphur ⁽³⁾

[0042] A, B, E, L, M, X, Y, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ are each asdefined above.

[0043] Including the various meanings (a), (b), (c), (d), (e), (f) and(g) of the group G, the following principal structures (I-3-B-a) to(I-3-B-g) result if W represents sulphur ⁽³⁾

[0044] in which

[0045] A, B, E, L, M, X, Y, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ are each asdefined above.

[0046] Furthermore, it has been found that the novel compounds of theformula (I) are obtained by one of the processes described below:

[0047] (A) Substituted 3-hetaryl-pyrrolidine-2,4-diones or enols thereofof the formulae (I-1-A-a) to (I-1-B-a)

[0048] (I-1-A-a) to (I-1-B-a)

[0049] in which

[0050] A, B, D and Het are each as defined above

[0051] are obtained when

[0052] N-acylamino acid esters of the formula (II)

[0053] in which

[0054] A, B, D and Het are each as defined above

[0055] and

[0056] R⁸ represents alkyl (preferably C₁-C₆-alkyl)

[0057] are condensed intramolecularly in the presence of a diluent andin the presence of a base.

[0058] (B) Moreover, it has been found that substituted3-hetaryl-4-hydroxy-Δ³-di-hydrofuranone derivatives of the formulae(I-2-A-a) to (I-2-B-a)

[0059] (I-2-A-a) to (I-2-B-a)

[0060] in which

[0061] A, B and Het are each as defined above

[0062] are obtained when

[0063] carboxylic esters of the formula (III)

[0064] in which

[0065] A, B, Het and R⁸ are each as defined above

[0066] are condensed intramolecularly in the presence of a diluent andin the presence of a base.

[0067] (C) Furthermore, it has been found that substituted3-hetaryl-4-hydroxy-Δ³-di-hydrothiophene-2-one derivatives of theformulae (I-3-A-a) to (I-3-B-a)

[0068] (I-3-A-a) to (I-3-B-a)

[0069] in which

[0070] A, B and Het are each as defined above

[0071] are obtained when

[0072] β-ketocarboxylic esters of the formula (IV)

[0073] in which

[0074] A, B, Het and R⁸ are each as defined above and

[0075] W¹ represents hydrogen, halogen, alkyl (preferably C₁-C₆-alkyl)or alkoxy (preferably C₁-C₈-alkoxy)

[0076] are cyclized intramolecularly, if appropriate in the presence ofa diluent and in the presence of an acid.

[0077] Moreover, it has been found

[0078] (D) that the compounds of the formulae (I-1-A-b) to (I-3-B-b)shown above, in which A, B, D, R¹ and Het are each as defined above, areobtained when compounds of the formulae (I-1-A-a) to (1-3-B-a) shownabove, in which A, B, D and Het are each as defined above, are in eachcase reacted

[0079] (α) with acyl halides of the formula (V)

[0080] in which

[0081] R¹ is as defined above and

[0082] Hal represents halogen (in particular chlorine or bromine) or

[0083] (β) with carboxylic anhydrides of the formula (VI)

R¹—CO—O—CO—R¹   (VI)

[0084] in which

[0085] R¹ is as defined above,

[0086] if appropriate in the presence of a diluent and if appropriate inthe presence of an acid binder;

[0087] (E) that the compounds of the formulae (I-1-A-c) to (I-3-B-c)shown above, in which A, B, D, R², M and Het are each as defined aboveand L represents oxygen, are obtained when compounds of the formulae(I-1-A-a) to (1-3-B-a) shown above, in which A B, D and Het are each asdefined above, are in each case reacted

[0088] with chloroformic esters or chloroformic thioesters of theformula (VII)

R²—M—CO—Cl   (VII)

[0089] in which

[0090] R² and M are each as defined above,

[0091] if appropriate in the presence of a diluent and if appropriate inthe presence of an acid binder;

[0092] (F) that the compounds of the formulae (I-1-A-c) to (I-3-B-c)shown above, in which A, B, D, R², M and Het are each as defined aboveand L represents sulphur, are obtained when compounds of the formulae(1-1-A-a) to (1-3-B-a) shown above, in which A, B, D and Het are each asdefined above, are in each case reacted

[0093] with chloromonothioformic esters or chlorodithioformic esters ofthe formula (VIII)

[0094] in which

[0095] M and R² are each as defined above,

[0096] if appropriate in the presence of a diluent and if appropriate inthe presence of an acid binder, and

[0097] (G) that compounds of the formulae (I-1-A-d) to (I-3-B-d) shownabove, in which A, B, D, R³ and Het are each as defined above, areobtained when compounds of the formulae (I-1-A-a) to (I-3-B-a) shownabove, in which A, B, D and Het are each as defined above, are in eachcase reacted

[0098] with sulphonyl chlorides of the formula (IX)

R³—SO₂—Cl   (IX)

[0099] in which

[0100] R³ is as defined above,

[0101] if appropriate in the presence of a diluent and if appropriate inthe presence of an acid binder,

[0102] (H) that compounds of the formulae (I-1-A-e) to (I-3-B-e) shownabove, in which A, B, D, L, R⁴, R⁵ and Het are each as defined above,are obtained when compounds of the formulae (I-1-A-a) to (I-3-B-a) shownabove, in which A, B, D and Het are each as defined above, are in eachcase reacted

[0103] with phosphorous compounds of the formula (X)

[0104] in which

[0105] L, R⁴ and R⁵ are each as defined above and

[0106] Hal represents halogen (in particular chlorine or bromine),

[0107] if appropriate in the presence of a diluent and if appropriate inthe presence of an acid binder,

[0108] (I) that compounds of the formulae (I-1-A-f) to (I-3-B-f) shownabove, in which A, B, D, E and Het are each as defined above, areobtained when compounds of the formulae (I-1-A-a) to (I-3-B-a), in whichA, B, D and Het are each as defined above, are in each case reacted

[0109] with metal compounds or amines of the formula (XI) or (XII)

[0110] in which

[0111] Me represents a mono- or divalent metal (preferably an alkalimetal or alkaline earth metal, such as lithium, sodium, potassium,magnesium or calcium),

[0112] t represents the number 1 or 2 and

[0113] R¹⁰, R¹¹, R¹² independently of one another each representhydrogen or alkyl (preferably C₁-C₈-alkyl),

[0114] if appropriate in the presence of a diluent,

[0115] (J) that compounds of the formulae (I-1-A-g) to (I-3-B-g) shownabove, in which A, B, D, L, R⁶, R⁷ and Het are each as defined above,are obtained when compounds of the formulae (I-1-A-a) to (I-3-B-a) shownabove, in which A, B, D and Het are each as defined above, are in eachcase reacted

[0116] (α) with isocyanates or isothiocyanates of the formula (XIII)

R⁶—N═C═L   (XIII)

[0117] in which

[0118] R⁶ and L are each as defined above,

[0119] if appropriate in the presence of a diluent and if appropriate inthe presence of a catalyst, or

[0120] (β) with carbamoyl chlorides or thiocarbamoyl chlorides of theformula (XIV)

[0121] in which

[0122] L, R⁶ and R⁷ are each as defined above,

[0123] if appropriate in the presence of a diluent and if appropriate inthe presence of an acid binder.

[0124] Furthermore, it has been found that the novel compounds of theformula (I) are highly active as pesticides, preferably as insecticides,acaricides and herbicides.

[0125] The formula (I) provides a general definition of the compoundsaccording to the invention. Preferred substituents or ranges of theradicals listed in the formulae mentioned above and below areillustrated below:

[0126] Het preferably represents

[0127] X preferably represents hydrogen, halogen, C₁-C₆-alkyl,C₁-C₄-halogenoalkyl, C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, nitro or cyano,

[0128] Y preferably represents halogen, C₁-C₆-alkyl,C₁-C₆-halogenoalkyl, C₁-C₆-alkoxy, C₁-C₆-halogenoalkoxy,C₁-C₆-alkylthio, C₁-C₆-alkylsulphonyl, C₁-C₆-alkylsulphoxinyl orrepresents the group

[0129] or in the case of Het=thiazolyl ((I-1-A) to (I-3-A)) alsorepresents

[0130] V¹ preferably represents hydrogen, halogen, C₁-C₁₂-alkyl,C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl,C₁-C₆-alkylsulphonyl, C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, nitro,cyano, phenoxy or represents phenyl, phenoxy, phenoxy-C₁-C₄-alkyl,phenyl-C₁-C₄-alkoxy, phenylthio-C₁-C₄-alkyl or phenyl-C₁-C₄-alkylthio,each of which is optionally mono- or polysubstituted by halogen,C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy,nitro or cyano,

[0131] V² and V³ independently of one another each preferably representhydrogen, halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl orC₁-C₄-halogenoalkoxy,

[0132] V¹ and V² together with the carbon atoms to which they areattached preferably represent an optionally C₁-C₄-alkyl- orhalogen-substituted saturated or unsaturated 5- or 6-membered cycle inwhich optionally one to three carbon atoms may be replaced by oxygen,sulphur or nitrogen,

[0133] W preferably represents N—D⁽¹⁾, oxygen⁽²⁾ or sulphur⁽³⁾,

[0134] A preferably represents hydrogen or in each case optionallyfluorine- or chlorine-substituted C₁-C₁₂-alkyl, C₃-C₈-alkenyl,C₁-C₆-alkoxy-C₁-C₆-alkyl, poly-C₁-C₆-alkoxy-C₁-C₆-alkyl,C₁-C₁₀-alkylthio-C₁-C₆-alkyl, optionally fluorine-, chlorine-,C₁-C₆-alkyl- or C₁-C₆-alkoxy-substituted C₃-C₈-cycloalkyl in whichoptionally one or two not directly adjacent ring members are replaced byoxygen and/or sulphur or represents in each case optionally halogen-,C₁-C₆-alkyl-, C₁-C₆-halogenoalkyl-, C₁-C₆-alkoxy-,C₁-C₆-halogenoalkoxy-, cyano- or nitro-substituted C₆- or C₁₀-aryl(phenyl or naphthyl), hetaryl having 5 or 6 ring atoms (for examplefuranyl, pyridyl, imidazolyl, triazolyl, pyrazolyl, pyrimidyl, thiazolylor thienyl) or C₆- or C₁₀-aryl-C₁-C₆-alkyl (phenyl-C₁-C₆-alkyl ornaphthyl-C₁-C₆-alkyl),

[0135] B preferably represents hydrogen, C₁-C₆-alkyl orC₁-C₄-alkoxy-C₁-C₄-alkly, or

[0136] A, B and the carbon atom to which they are attached preferablyrepresent saturated C₃-C₁₀-cycloalkyl or unsaturated C₅-C₁₀-cycloalkylin which optionally one ring member is replaced by oxygen or sulphur andwhich are optionally mono- or disubstituted by C₁-C₆-alkyl,C₃-C₈-cycloalkyl, C₁-C₄-halogenoalkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio,halogen or phenyl or

[0137] A, B and the carbon atom to which they are attached preferablyrepresent C₅-C₆-cycloalkyl which is substituted by an alkylenediyl groupwhich optionally contains an oxygen or sulphur atom, or by analkylenedioxyl or by an alkylenedithioyl group which, together with thecarbon atom to which it is attached, forms a further five- orsix-membered ring which may optionally be mono- to tetrasubstituted byC₁-C₄-alkyl, or

[0138] A, B and the carbon atom to which they are attached preferablyrepresent C₃-C₈-cycloalkyl or C₅-C₈-cycloalkenyl in which twosubstituents together with the carbon atoms to which they are attachedrepresent in each case optionally C₁-C₆-alkyl-, C₁-C₆-alkoxy- orhalogen-substituted C₂-C₆-alkanediyl, C₂-C₆-alkenediyl orC₄-C₆-alkanedienediyl in which optionally one methylene group isreplaced by oxygen or sulphur,

[0139] D preferably represents hydrogen, in each case optionallyhalogen- or cyano-substituted C₁-C₁₂-alkyl, C₃-C₈-alkenyl,C₃-C₈-alkinyl, C₁-C₁₀-alkoxy-C₂-C₈-alkyl, poly-C₁-C₈-alkoxy-C₂-C₈-alkyl,C₁-C₁₀-alkylthio-C₂-C₈-alkyl, optionally halogen-, C₁-C₄-alkyl-,C₁-C₄-alkoxy- or C₁-C₄-halogenoalkyl-substituted C₃-C₈-cycloalkyl inwhich optionally one ring member is replaced by oxygen or sulphur or ineach case optionally halogen-, C₁-C₆-alkyl-, C₁-C₆-halogenoalkyl,C₁-C₆-alkoxy-, C₁-C₆-halogenoalkoxy-, cyano- or nitro-substitutedphenyl, hetaryl having 5 or 6 ring atoms (for example furanyl,imidazolyl, pyridyl, thiazolyl, pyrazolyl, pyrimidyl, pyrrolyl, thienylor triazolyl), phenyl-C₁-C₆-alkyl or hetaryl-C₁-C₆-alkyl having 5 or 6ring atoms (for example furanyl, imidazolyl, pyridyl, thiazolyl,pyrazolyl, pyrimidyl, pyrrolyl, thienyl or triazolyl), or

[0140] A and D together preferably represent in each case optionallysubstituted C₃-C₆-alkanediyl or C₃-C₆-alkenediyl in which optionally onemethylene group is replaced by a carbonyl group, oxygen or sulphur,possible substituents being in each case:

[0141] halogen, hydroxyl, mercapto or in each case optionallyhalogen-substituted C₁-C₁₀-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio,C₃-C₇-cycloalkyl, phenyl or benzyloxy, or a further C₃-C₆-alkanediylgrouping, C₃-C₆-alkenediyl grouping or a butadienyl grouping which isoptionally substituted by C₁-C₆-alkyl or in which optionally twoadjacent substituents together with the carbon atoms to which they areattached form a further saturated or unsaturated cycle having 5 or 6ring atoms (in the case of the compounds of the formula (I-1-A) to(I-1-B), A and D together with the atoms to which they are attached inthis case represent, for example, the groups AD-1 to AD-10 mentionedfurther below) which may contain oxygen or sulphur, or which optionallycontains one of the groups below

[0142] G preferably represents hydrogen (a) or represents one of thegroups

[0143] E represents a metal ion equivalent or an ammonium ion,

[0144] L represents oxygen or sulphur and

[0145] M represents oxygen or sulphur,

[0146] R¹ preferably represents in each case optionallyhalogen-substituted C₁-C₂₀-alkyl, C₂-C₂₀-alkenyl,C₁-C₈-alkoxy-C₁-C₈-alkyl, C₁-C₈-alkylthio-C₁-C₈-alkyl,poly-C₁-C₈-alkoxy-C₁-C₈-alkyl or optionally halogen-, C₁-C₆-alkyl- orC₁-C₆-alkoxy-substituted C₃-C₈-cycloalkyl in which optionally one ormore (preferably not more than two) not directly adjacent ring membersare replaced by oxygen and/or sulphur,

[0147] represents optionally halogen-, cyano-, nitro-, C₁-C₆-alkyl,C₁-C₆-alkoxy-, C₁-C₆-halogenoalkyl-, C₁-C₆-halogenoalkoxy-,C₁-C₆-alkylthio- or C₁-C₆-alkylsulphonyl-substituted phenyl,

[0148] represents optionally halogen-, nitro-, cyano-, C₁-C₆-alkyl-,C₁-C₆-alkoxy-, C₁-C₆-halogenoalkyl- or C₁-C₆-halogenoalkoxy-substitutedphenyl-C₁-C₆-alkyl,

[0149] represents optionally halogen-, C₁-C₆-alkyl-,C₁-C₂-halogenoalkyl- or C₁-C₄-alkoxy-substituted 5- or 6-memberedhetaryl (for example pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanylor thienyl),

[0150] represents optionally halogen- or C₁-C₆-alkyl-substitutedphenoxy-C₁-C₆-alkyl or

[0151] represents optionally halogen-, amino- or C₁-C₆-alkyl-substituted5- or 6-membered hetaryloxy-C₁-C₆-alkyl (for example pyridyloxy-C₁-C₆-alkyl, pyrimidyloxy-C₁-C₆-alkyl or thiazolyloxy-C₁-C₆-alkyl),

[0152] R² preferably represents in each case optionallyhalogen-substituted C₁-C₂₀-alkyl, C₂-C₂₀-alkenyl,C₁-C₈-alkoxy-C₂-C₈-alkyl, poly-C₁-C₈-alkoxy-C₂-C₈-alkyl,

[0153] represents optionally halogen-, C₁-C₆-alkyl orC₁-C₆-alkoxy-substituted C₃-C₈-cycloalkyl in which optionally one ringatom is replaced by oxygen, or

[0154] represents in each case optionally halogen-, cyano-, nitro-,C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₆-halogenoalkyl- orC₁-C₆-halogenoalkoxy-substituted phenyl or benzyl,

[0155] R³ preferably represents optionally halogen-substitutedC₁-C₈-alkyl or represents in each case optionally halogen-,C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₄-halogenoalkyl-,C₁-C₄-halogenoalkoxy-, cyano- or nitro-substituted phenyl or benzyl,

[0156] R⁴ and R⁵ independently of one another each preferably representin each case optionally halogen-substituted C₁-C₈-alkyl, C₁-C₈-alkoxy,C₁-C₈-alkylamino, di-(C₁-C₈-alkyl)amino, C₁-C₈-alkylthio,C₂-C₈-alkenylthio, C₃-C₇-cycloalkylthio or represent in each caseoptionally halogen-, nitro-, cyano-, C₁-C₄-Alkoxy-,C₁-C₄-halogenoalkoxy-, C₁-C₄-alkylthio-, C₁-C₄-halogenoalkylthio-,C₁-C₄-alkyl- or C₁-C₄-halogenoalkyl-substituted phenyl, phenoxy orphenylthio,

[0157] R⁶ and R⁷ independently of one another each preferably representhydrogen, represent in each case optionally halogen-substitutedC₁-C₈-alkyl, C₃-C₈-cycloalkyl, C₁-C₈-alkoxy, C₃-C₈-alkenyl,C₁-C₈-alkoxy-C₁-C₈-alkyl, represent optionally halogen-,C₁-C₈-halogenoalkyl-, C₁-C₈-alkyl- or C₁-C₈-alkoxy-substituted phenyl,optionally halogen-, C₁-C₈-alkyl-, C₁-C₈-halogenoalkyl- orC₁-C₈-alkoxy-substituted benzyl or together represent an optionallyC₁-C₄-alkyl-substituted C₃-C₆-alkylene radical in which optionally onecarbon atom is replaced by oxygen or sulphur,

[0158] R¹³ preferably represents hydrogen, represents in each caseoptionally halogen-substituted C₁-C₈-alkyl or C₁-C₈-alkoxy, representsoptionally halogen-, C₁- C₄-alkyl- or C₁-C₄-alkoxy-substitutedC₃-C₈-cycloalkyl, in which optionally one methylene group is replaced byoxygen or sulphur, or represents in each case optionally halogen-,C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₄-halogenoalkyl-,C₁-C₄-halogenoalkoxy-, nitro- or cyano-substituted phenyl,phenyl-C₁-C₄-alkyl or phenyl-C₁-C₄-alkoxy,

[0159] R¹⁴ preferably represents hydrogen or C₁-C₈-alkyl or

[0160] R¹³ and R¹⁴ together preferably represent C₄-C₆-alkanediyl,

[0161] R¹⁵ and R¹⁶ are identical or different and each preferablyrepresent C₁-C₆-alkyl or

[0162] R¹⁵ and R¹⁶ together preferably represent a C₂-C₄-alkanediylradical which is optionally substituted by C₁-C₆-alkyl,C₁-C₆-halogenoalkyl or by optionally halogen-, C₁-C₆-alkyl-,C₁-C₄-halogenoalkyl-, C₁-C₆-alkoxy-, C₁-C₄-halogenoalkoxy-, nitro- orcyano-substituted phenyl,

[0163] R¹⁷ and R¹⁸ independently of one another each preferablyrepresent hydrogen, represent optionally halogen-substituted C₁-C₈-alkylor represent optionally halogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-,C₁-C₄-halogenoalkyl-, C₁-C₄-halogenoalkoxy-, nitro- or cyano-substitutedphenyl or

[0164] R¹⁷ and R¹⁸ together with the carbon atom to which they areattached preferably represent a carbonyl group or represent optionallyhalogen-, C₁-C₄-alkyl or C₁-C₄-alkoxy-substituted C₅-C₇-cycloalkyl inwhich optionally one methylene group is replaced by oxygen or sulphur,

[0165] R¹⁹ and R²⁰ independently of one another each preferablyrepresent C₁-C₁₀-alkyl, C₂-C₁₀-alkenyl, C₁-C₁₀-alkoxy,C₁-C₁₀-alkylamino, C₃-C₁₀-alkenylamino, di-(C₁-C₁₀-alkyl)amino ordi-(C₃-C₁₀-alkenyl)amino.

[0166] In the radical definitions mentioned as being preferred, halogenrepresents fluorine, chlorine, bromine and iodine, in particularfluorine, chlorine and bromine.

[0167] Het particularly preferably represents

[0168] X particularly preferably represents hydrogen, chlorine, bromine,C₁-C₄-alkyl, C₁-C₂-halogenoalkyl, nitro or cyano,

[0169] Y particularly preferably represents chlorine, bromine,C₁-C₄-alkyl, C₁-C₄-halogenoalkyl, C₁-C₄-alkoxy, C₁-C₄-halogenoalkoxy,C₁-C₄-alkylthio, C₁-C₄-alkylsulphonyl or represents the group

[0170] or in the case of Het=thiazolyl ((I-1-A) to (I-3-A)) alsorepresents

[0171] V¹ particularly preferably represents hydrogen, fluorine,chlorine, bromine, C₁-C₆-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl,C₁-C₂-halogenoalkoxy, nitro, cyano, phenoxy or represents phenyl,phenoxy, phenoxy-C₁-C₂-alkyl, phenyl-C₁-C₂-alkoxy,phenylthio-C₁-C₂-alkyl or phenyl-C₁-C₂-alkylthio, each of which isoptionally mono- or disubstituted by fluorine, chlorine, bromine,C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl, C₁-C₂-halogenoalkoxy,nitro or cyano,

[0172] V² particularly preferably represents hydrogen, fluorine,chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl orC₁-C₂-halogenoalkoxy, or

[0173] V¹ and V² together with the carbon atoms to which they areattached particularly preferably represent an optionally fluorine- ormethyl-substituted 5- or 6-membered cycle in which optionally one or twocarbon atoms may be replaced by oxygen,

[0174] W particularly preferably represents N—D⁽¹⁾, oxygen⁽²⁾ orsulphur⁽³⁾,

[0175] A particularly preferably represents hydrogen, in each caseoptionally fluorine-substituted C₁-C₁₀-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,optionally fluorine-, chlorine-, C₁-C₄-alkyl- orC₁-C₄-alkoxy-substituted C₃-C₇-cycloalkyl in which optionally one ringmember is replaced by oxygen or sulphur or in each case optionallyfluorine-, chlorine-, bromine-, C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-,C₁-C₄-alkoxy- or C₁-C₄-halogenoalkoxy-substituted phenyl orphenyl-C₁-C₂-alkyl,

[0176] B particularly preferably represents hydrogen or C₁-C₄-alkyl, or

[0177] A, B and the carbon atom to which they are attached particularlypreferably represent saturated C₅-C₇-cycloalkyl in which optionally onering member is replaced by oxygen or sulphur and which is optionallymono- or disubstituted by C₁-C₆-alkyl, C₅-C₆-cycloalkyl,C₁-C₂-halogenoalkyl, C₁-C₆-alkoxy, fluorine, chlorine or phenyl or

[0178] A, B and the carbon atom to which they are attached particularlypreferably represent C₅-C₆-cycloalkyl which is substituted by analkylenediyl group which optionally contains an oxygen or sulphur atomor by an alkylenedioxyl or by an alkylenedithioyl group which togetherwith the carbon atom to which it is attached forms a further five- orsix-membered ring which may optionally be mono- to trisubstituted byC₁-C₃-alkyl, or

[0179] A, B and the carbon atom to which they are attached particularlypreferably represent C₅-C₆-cycloalkyl or C₅-C₆-cycloalkenyl in which twosubstituents together with the carbon atoms to which they are attachedrepresent in each case optionally C₁-C₅-alkyl-, C₁-C₅-alkoxy-,fluorine-, chlorine- or bromine-substituted C₂-C₄-alkanediyl,C₁-C₄-alkenediyl in which optionally one methylene group is replaced byoxygen or sulphur or represent butadienediyl,

[0180] D particularly preferably represents hydrogen, represents in eachcase optionally fluorine-substituted C₁-C₁₀-alkyl, C₃-C₆-alkenylC₁-C₆-alkoxy-C₂-C₄-alkyl or C₁-C₆-alkylthio-C₂-C₄-alkyl, representsoptionally fluorine-, C₁-C₄-alkyl, C₁-C₄-alkoxy orC₁-C₉-halogenoalkyl-substituted C₃-C₇-cycloalkyl, in which optionallyone methylene group is replaced by oxygen or sulphur or represents ineach case optionally fluorine-. chlorine-, bromine-, C₁-C₄-alkyl-,C₁-C₂-halogenoalkyl-, C₁-C₄-alkoxy- or C₁-C₂-halogenoalkoxy-substitutedphenyl or phenyl-C₁-C₄-alkyl, or

[0181] A and D together particularly preferably represent optionallysubstituted C₃-C₅-alkanediyl in which optionally one methylene group maybe replaced by a carbonyl group, oxygen or sulphur, possiblesubstituents being hydroxyl, C₁-C₆-alkyl or C₁-C₄-alkoxy, or

[0182] A and D together with the atoms to which they are attachedparticularly preferably represent one of the groups AD-1 to AD-10:

[0183] G particularly preferably represents hydrogen (a) or representsone of the groups

[0184] in particular (a), (b), (c) or (g),

[0185] in which

[0186] E represents a metal ion equivalent or an ammonium ion,

[0187] L represents oxygen or sulphur and

[0188] M represents oxygen or sulphur,

[0189] R¹ particularly preferably represents in each case optionallyfluorine- or chlorine-substituted C₁-C₁₆-alkyl, C₂-C₁₆-alkenyl,C₁-C₆-alkoxy-C₁-C₄-alkyl, C₁-C₆-alkylthio-C₁-C₄-alkyl or optionallyfluorine-, chlorine-, C₁-C₅-alkyl- or C₁-C₅-alkoxy-substitutedC₃-C₇-cycloalkyl in which optionally one or two not directly adjacentring members are replaced by oxygen and/or sulphur,

[0190] represents optionally fluorine-, chlorine-, bromine-, cyano-,nitro-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-, C₁-C₃-halogenoalkyl-,C₁-C₃-halogenoalkoxy-, C₁-C₄-alkylthio- orC₁-C₄-alkylsulphonyl-substituted phenyl,

[0191] represents optionally fluorine-, chlorine-, bromine-,C₁-C₄-alkyl-, C₁-C₄-alkoxy-, C₁-C₃-halogenoalkyl- orC₁-C₃-halogenoalkoxy-substituted phenyl-C₁-C₄-alkyl,

[0192] represents in each case optionally fluorine-, chlorine-,bromine-, C₁-C₄-alkyl-, trifluoromethyl- or C₁-C₂-alkoxy-substitutedpyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl or thienyl,

[0193] R² particularly preferably represents in each case optionallyfluorine-substituted C₁-C₁₆-alkyl, C₂-C₁₆-alkenyl orC₁-C₆-alkoxy-C₂-C₆-alkyl,

[0194] represents optionally fluorine-, chlorine-, C₁-C₄-alkyl- orC₁-C₄-alkoxy-substituted C₃-C₇-cycloalkyl or

[0195] represents in each case optionally fluorine-, chlorine-,bromine-, cyano-, nitro-, C₁-C₄-alkyl-, C₁-C₃-alkoxy-,C₁-C₂-halogenoalkyl- or C₁-C₂-halogenoalkoxy-substituted phenyl orbenzyl,

[0196] R³ particularly preferably represents optionallyfluorine-substituted C₁-C₆-alkyl or represents optionally fluorine-,chlorine-, bromine-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-, C₁-C₃-halogenoalkyl-,C₁-C₃-halogenoalkoxy-, cyano- or nitro-substituted phenyl,

[0197] R⁴ particularly preferably represents C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₆-alkylamino, di-(C₁-C₆-alkyl)amino, C₁-C₆-alkylthio,C₃-C₄-alkenylthio, C₃-C₆-cycloalkylthio or represents in each caseoptionally fluorine-, chlorine-, bromine-, nitro-, cyano-,C₁-C₃-alkoxy-, C₁-C₃-halogenoalkoxy-, C₁-C₃-alkylthio-,C₁-C₃-halogenoalkylthio-, C₁-C₃-alkyl- orC₁-C₃-halogenoalkyl-substituted phenyl, phenoxy or phenylthio,

[0198] R⁵ particularly preferably represents C₁-C₆-alkoxy orC₁-C₆-alkylthio,

[0199] R⁶ particularly preferably represents C₁-C₆-alkyl,C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₃-C₆-alkenyl, C₁-C₆-alkoxy-C₁-C₆-alkyl,represents optionally fluorine-, chlorine-, bromine-,C₁-C₃-halogenoalkyl-, C₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted phenyl,represents optionally fluorine-, chlorine-, bromine-, C₁-C₄-alkyl-,C₁-C₃-halogenoalkyl- or C₁-C₄-alkoxy-substituted benzyl,

[0200] R⁷ particularly preferably represents hydrogen, C₁-C₆-alkyl,C₃-C₆-alkenyl, or

[0201] R⁶ and R⁷ together particularly preferably represent anoptionally methyl- or ethyl-substituted C₄-C₅-alkylene radical in whichoptionally one methylene group is replaced by oxygen or sulphur.

[0202] In the radical definitions mentioned as being particularlypreferred, halogen represents fluorine, chlorine, bromine and iodine, inparticular fluorine, chlorine and bromine.

[0203] Het very particularly preferably represents

[0204] X very particularly preferably represents hydrogen, chlorine,bromine, methyl, ethyl, n-propyl, iso-propyl, n-butyl or iso-butyl,

[0205] Y very particularly preferably represents methyl, ethyl,n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, trifluoromethyl orrepresents the group

[0206] or in the case of Het=thiazolyl ((I-1-A) to (I-3-A)) alsorepresents

[0207] V¹ very particularly preferably represents hydrogen, fluorine,chlorine, bromine, methyl, ethyl, n-propyl, iso-propyl, n-butyl,iso-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy,trifluoromethyl, trifluoromethoxy, nitro, cyano, phenoxy or phenyl whichis optionally mono- or disubstituted by fluorine, chlorine, methyl,methoxy, trifluoromethyl or trifluoromethoxy,

[0208] V² very particularly preferably represents hydrogen, fluorine,chlorine, methyl, ethyl, n-propyl, iso-propyl, methoxy, ethoxy,trifluoromethyl or trifluoromethoxy, or

[0209] V¹ and V² together very particularly preferably represent—O—CH₂—O—, —O—CF₂—O— or —O—CF₂—CF₂—O—,

[0210] W very particularly preferably represents N—D⁽¹⁾, oxygen⁽²⁾ orsulphur⁽³⁾,

[0211] A very particularly preferably represents hydrogen, represents ineach case optionally fluorine-substituted C₁-C₈-alkyl orC₁-C₄-alkoxy-C₁-C₂-alkyl, optionally fluorine-, methyl-, ethyl- ormethoxy-substituted C₃-C₆-cycloalkyl in which optionally one ring memberis replaced by oxygen or sulphur or represents in each case optionallyfluorine-, chlorine-, bromine-, methyl-, ethyl-, n-propyl-, iso-propyl-,tert-butyl-, methoxy-, ethoxy-, trifluoromethyl-, trifluoromethoxy-,cyano- or nitro-substituted phenyl or benzyl,

[0212] B very particularly preferably represents hydrogen, methyl orethyl, or

[0213] A, B and the carbon atom to which they are attached veryparticularly preferably represent saturated C₅-C₆-cycloalkyl in whichoptionally one ring member is replaced by oxygen or sulphur and which isoptionally mono- or disubstituted by methyl, ethyl, propyl, isopropyl,butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, methoxy,ethoxy, propoxy, iso-propoxy, butoxy or iso-butoxy or

[0214] A, B and the carbon atom to which they are attached veryparticularly preferably represent C₆-cycloalkyl which is substituted byan alkylenedioxyl group which is optionally mono- or disubstituted bymethyl or ethyl and which together with the carbon atom to which it isattached forms a further five- or six-membered ring or

[0215] A, B and the carbon atom to which they are attached veryparticularly preferably represent C₅-C₆-cycloalkyl or C₅-C₆-cycloalkenylin which two substituents together with the carbon atoms to which theyare attached represent C₂-C₄-alkanediyl or C₂-C₄-alkenediyl in which ineach case optionally one methylene group is replaced by oxygen orsulphur, or represent butadienediyl,

[0216] D very particularly preferably represents hydrogen, represents ineach case optionally fluorine-substituted C₁-C₆-alkyl, C₃-C₄-alkenyl,C₁-C₄-alkoxy-C₂-C₃-alkyl, C₁-C₄-alkylthio-C₂-C₃-alkyl orC₃-C₆-cycloalkyl in which optionally one methylene group is replaced byoxygen or sulphur or represents in each case optionally fluorine-,chlorine-, methyl-, ethyl-, n-propyl-, iso-propyl-, methoxy-, ethoxy-,trifluoromethyl- or trifluoromethoxy-substituted phenyl or benzyl, or

[0217] A and D together very particularly preferably representoptionally substituted C₃-C₄-alkanediyl in which optionally one carbonatom is replaced by oxygen or sulphur and which is optionallysubstituted by methyl or

[0218] A and D together with the atoms to which they are attached veryparticularly preferably represent one of the groups AD below:

[0219] G very particularly preferably represents hydrogen (a) orrepresents one of the groups

[0220] in particular (a), (b) or (c),

[0221] in which

[0222] E represents a metal ion equivalent or an ammonium ion,

[0223] L represents oxygen or sulphur and

[0224] M represents oxygen or sulphur,

[0225] R¹ very particularly preferably represents in each caseoptionally fluorine-substituted C₁-C₁₄-alkyl, C₂-C₁₄-alkenyl,C₁-C₄-alkoxy-C₁-C₂-alkyl, C₁-C₄-alkylthio-C₁-C₁-alkyl or in each caseoptionally fluorine-, chlorine-, methyl-, ethyl- or methoxy-substitutedcyclopropyl, cyclopentyl or cyclohexyl,

[0226] represents phenyl which is optionally mono- or disubstituted byfluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, tert-butyl,methoxy, ethoxy, trifluoromethyl or trifluoromethoxy,

[0227] represents thienyl or pyridyl, each of which is optionallymonosubstituted by fluorine, chlorine, bromine or methyl,

[0228] R² very particularly preferably represents in each caseoptionally fluorine-substituted C₁-C₈-alkyl, C₂-C₈-alkenyl orC₁-C₄-alkoxy-C₂-C₃-alkyl,

[0229] represents optionally fluorine-, chlorine-, methyl-, ethyl-,n-propyl-, iso-propyl- or methoxy-substituted cyclohexyl,

[0230] or represents in each case optionally fluorine-, chlorine-,cyano-, nitro-, methyl-, ethyl-, methoxy-, trifluoromethyl- ortrifluoromethoxy-substituted phenyl or benzyl,

[0231] R³ very particularly preferably represents methyl, ethyl.n-propyl or represents phenyl which is optionally monosubstituted byfluorine, chlorine, bromine, methyl, tert-butyl, methoxy,trifluoromethyl, trifluoromethoxy, cyano or nitro,

[0232] R⁴ very particularly preferably represents C₁-C₄-alkyl,C₁-C₄-alkoxy, C₁-C₄-alkylamino, di-(C₁-C₄-alkyl)amino, C₁-C₄-alkylthioor represents in each case optionally fluorine-, chlorine-, bromine-,nitro-, cyano-, C₁-C₂-alkoxy-, C₁-C₂-fluoroalkoxy-, C₁-C₂-alkylthio-,C₁-C₂-fluoroalkylthio- or C₁-C₃-alkyl-substituted phenyl, phenoxy orphenylthio,

[0233] R⁵ very particularly preferably represents methoxy, ethoxy,methylthio or ethylthio,

[0234] R⁶ very particularly preferably represents C₁-C₄-alkyl,C₃-C₆-cycloalkyl, C₁-C₄-alkoxy, C₃-C₄-alkenyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,represents optionally fluorine-, chlorine-, bromine-, trifluoromethyl-,methyl- or methoxy-substituted phenyl, represents optionally fluorine-,chlorine-, bromine-, methyl-, trifluoromethyl- or methoxy-substitutedbenzyl,

[0235] R⁷ very particularly preferably represents hydrogen, methyl,ethyl, propyl or allyl, or

[0236] R⁶ and R⁷ together very particularly preferably represent aC₅-C₆-alkylene radical in which optionally one methylene group isreplaced by oxygen or sulphur.

[0237] Het with particular preference represents

[0238] X with particular preference represents hydrogen, chlorine,bromine, methyl, ethyl, n-propyl, or iso-propyl,

[0239] Y with particular preference represents methyl, ethyl, n-propyl,i-propyl, n-butyl, i-butyl, tert-butyl, trifluoromethyl or representsthe group

[0240] or in the case of Het=thiazolyl ((I-1-A) or (I-3-A)) alsorepresents

[0241] V¹ with particular preference represents hydrogen, fluorine,chlorine, bromine, methyl, ethyl, n-propyl, iso-propyl, n-butyl,iso-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy,trifluoromethyl, trifluoromethoxy, phenoxy, represents optionallychlorine- or trifluoromethyl-substituted phenyl,

[0242] V² with particular preference represents hydrogen, fluorine,chlorine, methyl, ethyl, methoxy or trifluoromethyl, or

[0243] V¹ and V² together with particular preference represent —O—CH₂—O—or —O—CF₂—O—,

[0244] W with particular preference represents N—D⁽¹⁾, oxygen⁽²⁾ orsulphur⁽³⁾,

[0245] A with particular preference represents hydrogen or C₁-C₄-alkylor cyclopropyl,

[0246] B with particular preference represents hydrogen or methyl, or

[0247] A, B and the carbon atom to which they are attached withparticular preference represent saturated C₅-C₆-cycloalkyl in whichoptionally one ring member is replaced by oxygen or sulphur, and whichis optionally mono- or disubstituted by methyl, ethyl, propyl,isopropyl, trifluoromethyl, methoxy, ethoxy, propoxy, butoxy oriso-butoxy, or represents C₅-C₆-cycloalkyl in which two not directlyadjacent carbon atoms form a further five-membered ring,

[0248] D with particular preference represents hydrogen,

[0249] D also with particular preference represents i-propyl,

[0250] A and D together with the atoms to which they are attached withparticular preference represent cyclohexyl in which one ring atom may bereplaced by sulphur,

[0251] G with particular preference represents hydrogen (a) or in thecase of Het=thiazolyl ((I-1-A) to (I-3-A)) (represents) one of thegroups

[0252] in which

[0253] L represents oxygen and

[0254] M represents oxygen,

[0255] R¹ with particular preference represents in each case optionallyfluorine- or chlorine-substituted C₁-C₄-alkyl, C₂-C₄-alkenyl,C₁-C₄-alkoxy-C₁-C₂-alkyl, C₁-C₄-alkylthio-C₁-C₂-alkyl or optionallyfluorine-, chlorine-, methyl-, ethyl- or methoxy-substituted cyclopropylor cyclohexyl,

[0256] represents phenyl which is optionally monosubstituted byfluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl,i-propyl, tert-butyl, methoxy, ethoxy, i-propoxy, tert-butoxy,trifluoromethyl or trifluoromethoxy,

[0257] represents thienyl or pyridyl, each of which is optionallymonosubstituted by chlorine or methyl,

[0258] R² with particular preference represents optionally in each casefluorine-substituted C₁-C₄-alkyl, C₂-C₄-alkenyl orC₁-C₄-alkoxy-C₂-C₃-alkyl,

[0259] represents optionally methyl-, ethyl-, n-propyl-, iso-propyl- ormethoxy-substituted cyclohexyl,

[0260] or represents phenyl or benzyl, each of which is optionallymonosubstituted by fluorine, chlorine, cyano, nitro, methyl, ethyl,methoxy, trifluoromethyl or trifluoromethoxy,

[0261] Het especially preferably represents

[0262] X especially preferably represents methyl, ethyl, n-propyl,i-propyl, chlorine or bromine,

[0263] Y especially preferably represents methyl, ethyl, n-propyl ori-propyl or represents the groups

[0264] in which

[0265] V¹ especially preferably represents hydrogen, bromine, chlorine,methyl, trifluoromethyl, phenoxy or t-butyl or represents optionallychlorine- or trifluoromethyl-substituted phenyl,

[0266] V² especially preferably represents hydrogen, chlorine, fluorineor methoxy or

[0267] V¹ and V² together especially preferably represent —O—CH₂—O— or—O—CF₂—O—,

[0268] W especially preferably represents N—D⁽¹⁾, oxygen⁽²⁾ orsulphur⁽³⁾,

[0269] D especially preferably represents hydrogen or i-propyl(especially hydrogen),

[0270] A especially preferably represents methyl, ethyl, n- or i-propylor cyclopropyl or hydrogen (especially methyl),

[0271] B especially preferably represents hydrogen or methyl, or

[0272] A and B and the carbon atom to which they are attached especiallypreferably represent cyclohexyl in which optionally one ring atom isreplaced by oxygen and which is optionally mono- or disubstituted bymethyl, ethyl, methoxy or ethoxy, or represent cyclohexyl in which twonot directly adjacent carbon atoms form a further 5-membered C ring,

[0273] A and D together with the atoms to which they are attachedespecially preferably represent cyclohexyl in which one ring atom may bereplaced by sulphur,

[0274] G especially preferably represents hydrogen (a) or represents oneof the groups

[0275] in which

[0276] R¹ especially preferably represents methyl, ethyl, n-propyl ori-propyl or represents in each case optionally chlorine-substitutedphenyl or pyridyl,

[0277] R² especially preferably represents methyl, ethyl, phenyl,benzyl, n- or i-propyl.

[0278] Het especially preferably represents

[0279] X especially preferably represents methyl or ethyl,

[0280] Y especially preferably represents optionallychlorine-substituted phenyl,

[0281] A especially preferably represents methyl, ethyl, n- or i-propyl,

[0282] B especially preferably represents methyl, or

[0283] A and B and the carbon atom to which they are attached togetherespecially preferably represent cyclohexyl which is optionallysubstituted by methoxy or methyl,

[0284] W especially preferably represents N—D or oxygen,

[0285] D especially preferably represents hydrogen,

[0286] G especially preferably represents hydrogen.

[0287] The abovementioned general or preferred radical definitions orillustrations can be combined with one another as desired, i.e.including combinations between the respective ranges and preferredranges. They apply both to the end products and, correspondingly, to theprecursors and intermediates.

[0288] Preference according to the invention is given to the compoundsof the formula (I) which contain a combination of the meanings listedabove as being preferred (preferable).

[0289] Particular preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningslisted above as being particularly preferred.

[0290] Very particular preference according to the invention is given tothe compounds of the formula (I) which contain a combination of themeanings listed above as being very particularly preferred.

[0291] Particular preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningslisted above as being with particular preference.

[0292] A special preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningslisted above as being especially preferred.

[0293] Saturated or unsaturated hydrocarbon radicals, such as alkyl oralkenyl, can in each case be straight-chain or branched as far as thisis possible, including in combination with heteroatoms, such as, forexample, in alkoxy.

[0294] Unless indicated otherwise, optionally substituted radicals canbe mono- or polysubstituted, where in the case of polysubstitutions, thesubstituents can be identical or different.

[0295] In addition to the compounds mentioned in the PreparationExamples, the following compounds of the formula (I-1-a) may, forexample, be mentioned specifically:

[0296] X=CH₃,V=3-Cl, V²=H. TABLE 1 A B D CH₃ H H C₂H₅ H H C₃H₇ H Hi-C₃H₇ H H C₄H₉ H H i-C₄H₉ H H s-C₄H₉ H H t-C₄H₉ H H CH₃ CH₃ H C₂H₅ CH₃H C₃H₇ CH₃ H i-C₃H₇ CH₃ H C₄H₉ CH₃ H i-C₄H₉ CH₃ H s-C₄H₉ CH₃ H t-C₄H₉CH₃ H

CH₃ H

CH₃ H

CH₃ H —(CH₂)₂— H —(CH₂)₄— H —(CH₂)₅— H —(CH₂)₆— H A D B —(CH₂)₇— H—(CH₂)₂—O—(CH₂)₂— H —CH₂—O—(CH₂)₃— H —(CH₂)₂—S—(CH₂)₂— H—CH₂—CHCH₃—(CH₂)₃— H —(CH₂)₂—CHCH₃—(CH₂)₂— H —(CH₂)₂—CHC₂H₅—(CH₂)₂— H—(CH₂)₂—CHC₃H₇—(CH₂)₂— H —(CH₂)₂—CHi—C₃H₇—(CH₂)₂— H—(CH₂)₂—CHOCH₃—(CH₂)₂— H —(CH₂)₂—CHOC₂H₅—(CH₂)₂— H—(CH₂)₂—CHOC₃H₇—(CH₂)₂— H —(CH₂)₂—CHi—C₃H₇—(CH₂)₂— H—(CH₂)₂—C(CH₃)₂—(CH₂)₂— H —CH₂—(CHCH₃)₂—(CH₂)₂— H

H

H

H

H

H —(CH₂)₃— H —(CH₂)₄— H —CH₂—CHCH₃—CH₂— H —CH₂—CH₂—CHCH₃— H—CH₂—CHCH₃—CHCH₃— H —CH₂—S—CH₂— H —CH₂—S—(CH₂)₂— H —(CH₂)₂—S—CH₂— H

H H CH₃ H H C₂H₅ H H C₃H₇ H H i-C₃H₇ H H

H H

H H

H CH₃ CH₃ H CH₃ C₂H₅ H CH₃ C₃H₇ H CH₃ i-C₃H₇ H CH₃

H CH₃

H CH₃

H C₂H₅ CH₃ H C₂H₅ C₂H₅ H

[0297] TABLE 2 A, B and D are as stated in Table 1 X = CH₃; V¹ = 4-Cl;V² = H.

[0298] TABLE 3 A, B and D are as stated in Table 1 X = CH₃; V¹ = 3-CF₃;V² = H.

[0299] TABLE 4 A, B and D are as stated in Table 1 X = CH₃; V¹ = 4-CF₃;V² = H.

[0300] TABLE 5 A, B and D are as stated in Table 1 X = CH₃; V¹ = 4-Cl;V² = 2-Cl.

[0301] TABLE 6 A, B and D are as stated in Table 1 X = CH₃; V¹ = 4-Cl;V² = 3-Cl.

[0302] TABLE 7 A, B and D are as stated in Table 1 X = CH₃;V¹ = 4-CH₃;V² = H.

[0303] TABLE 8 A, B and D are as stated in Table 1 X = CH₃; V¹ = 2-Cl;V² = 6-OCH₃.

[0304] TABLE 9 A, B and D are as stated in Table 1 X = C₂H₅; V¹ = 4-Cl;V² = H.

[0305] TABLE 10 A, B and D are as stated in Table 1 X = C₃H₇; V¹ = 4-Cl;V² = H.

[0306] TABLE 11 A, B and D are as stated in Table 1 X = C₂H₅; V¹ = 3-Cl;V² = H

[0307] TABLE 12 A, B and D are as stated in Table 1 X = C₃H₇; V¹ = 3-Cl;V² = H.

[0308] TABLE 13 A, B and D are as stated in Table 1 X = C₂H₅; V¹ =4-CF₃; V² = H.

[0309] TABLE 14 A, B and D are as stated in Table 1 X = C₂H₅; V¹ =3-CF₃; V² = H.

[0310] TABLE 15 A, B and D are as stated in Table 1 X = C₃H₇; V¹ =4-CF₃; V² = H.

[0311] TABLE 16 A, B and D are as stated in Table 1 X = C₃H₇; V¹ =3-CF₃; V² = H.

[0312] TABLE 17 A, B and D are as stated in Table 1 X = Cl; V¹ = 4-Cl;V² = H.

[0313] TABLE 18 A, B and D are as stated in Table 1 X = Br; V¹ = 4-Cl;V² = H.

[0314] TABLE 19 A, B and D are as stated in Table 1 X = C₂H₅; V¹ = 3-Cl;V² = 4-Cl.

[0315] TABLE 20 A, B and D are as stated in Table 1 X = C₃H₇; V¹ = 3-Cl;V² = 4-Cl.

[0316] TABLE 21 A, B and D are as stated in Table 1 X = CH₃; V¹ = 4-Br;V² = H.

[0317] In addition to the compounds mentioned in the PreparationExamples, the following compounds of the formula (I-2-a) may, forexample, be mentioned specifically:

TABLE 22 X = CH₃, V¹ = 3-Cl, V² = H. A B CH₃ H C₂H₅ H C₃H₇ H i-C₃H₇ HC₄H₉ H i-C₄H₉ H s-C₄H₉ H t-C₄H₉ H CH₃ CH₃ C₂H₅ CH₃ C₃H₇ CH₃ i-C₃H₇ CH₃C₄H₉ CH₃ i-C₄H₉ CH₃ s-C₄H₉ CH₃ t-C₄H₉ CH₃

CH₃

CH₃

CH₃ —(CH₂)₂— —(CH₂)₄— —(CH₂)₅— —(CH₂)₆— —(CH₂)₇— —(CH₂)₂—O—(CH₂)₂——CH₂—O—(CH₂)₃— —(CH₂)₂—S—(CH₂)₂— —CH₂—CHCH₃—(CH₂)₃——(CH₂)₂—CHCH₃—(CH₂)₂— (CH₂)₂—CHC₂H₅—(CH₂)₂— —(CH₂)₂—CHC₃H₇—(CH₂)₂——(CH₂)₂—CHi—C₃H₇—(CH₂)₂— —(CH₂)₂—CHOCH₃—(CH₂)₂— —(CH₂)₂—CHOC₂H₅—(CH₂)₂——(CH₂)₂—CHOC₃H₇—(CH₂)₂— —(CH₂)₂—CHi—C₃H₇—(CH₂)₂— —(CH₂)₂—C(CH₃)₂—(CH₂)₂——CH₂—(CHCH₃)₂—(CH₂)₂—

[0318] TABLE 23 A and B are as stated in Table 22 X = CH₃; V¹ = 4-Cl; V²= H.

[0319] TABLE 24 A and B are as stated in Table 22 X = CH₃; V¹ = 3-CF₃;V² = H.

[0320] TABLE 25 A and B are as stated in Table 22 X = CH₃; V¹ = 4-CF₃;V² = H.

[0321] TABLE 26 A and B are as stated in Table 22 X = CH ₃; V¹ = 4-Cl;V² = 2-Cl.

[0322] TABLE 27 A and B are as stated in Table 22 X = CH₃; V¹ = 4-Cl; V²= 3-Cl.

[0323] TABLE 28 A and B are as stated in Table 22 X = CH₃; V¹ = 4-CH₃;V² = H.

[0324] TABLE 29 A and B are as stated in Table 22 X = CH₃; V¹ = 2-Cl; V²= 6-OCH₃.

[0325] TABLE 30 A and B are as stated in Table 22 X = C₂H₅; V¹ = 4-Cl;V² = H.

[0326] TABLE 31 A and B are as stated in Table 22 X = C₃H₇; V¹ = 4-Cl;V² = H.

[0327] TABLE 32 A and B are as stated in Table 22 X = C₂H₅; V¹ = 3-Cl;V² = H.

[0328] TABLE 33 A and B are as stated in Table 22 X = C₃H₇; V¹ = 3-Cl;V² = H.

[0329] TABLE 34 A and B are as stated in Table 22 X = C₂H₅; V¹ =4-CF_(3; V) ² =H

[0330] TABLE 35 A and B are as stated in Table 22 X = C₃H₇; V¹ = 4-CF₃;V² = H.

[0331] TABLE 36 A and B are as stated in Table 22 X = C₂H₅; V¹ = 3-CF₃;V¹ = H.

[0332] TABLE 37 A and B are as stated in Table 22 X = C₃H₇; V¹= 3-CF₃;V² = H.

[0333] TABLE 38 A and B are as stated in Table 22 X = Cl; V¹ = 4-Cl; V²= H.

[0334] TABLE 39 A and B are as stated in Table 22 X = Br; V¹ = 4-Cl; V²= H.

[0335] TABLE 40 A and B are as stated in Table 22 X = C₂H₅; V¹ = 3-Cl;V² = 4-Cl.

[0336] TABLE 41 A and B are as stated in Table 22 X = C₃H₇; V¹ = 3-Cl;V² = 4-Cl.

[0337] TABLE 42 A and B are as stated in Table 22 X = CH₃; V¹ = 4-Br; V²= H.

[0338] Using, according to process (A), ethylN-[4-(5-methyl-2-phenyl)-thiazolylacetyl]-1-amino-cyclohexane-carboxylateas starting material, the course of the process according to theinvention can be represented by the following equation:

[0339] Using, according to process (B), ethylO-[4-(5-methyl-2-(4-chloro)-phenyl)-thiazolyl-acetyl]-2-hydroxyisobutyrateas starting material, the course of the process according to theinvention can be represented by the following equation:

[0340] Using, according to process (C), ethyl2-[4-(5-methyl-2-phenyl)-thiazolyl]-4-(4-methoxy)-benzylmercapto-4-methyl-3-oxo-valerateas starting material, the course of the process according to theinvention can be represented by the following equation:

[0341] Using, according to process (Dα),3-[4-(5-methyl-2-(3-chloro-phenyl)-thiazolyl]-5,5-dimethylpyrrolidine-2,4-dioneand pivaloyl chloride as starting materials, the course of the processaccording to the invention can be represented by the following equation:

[0342] Using, according to process (Dβ),3-[4-(5-ethyl-2-(4-methoxy-phenyl))-thiazolyl]-4-hydroxy-5-phenyl-Δ³-dihydrofuran-2-oneand acetic anhydride as starting materials, the course of the processaccording to the invention can be represented by the following equation:

[0343] Using, according to process (E),3-[4-(5-methyl-2-phenyl)-thiazolyl]-5,5-dimethylpyrrolidine-2,4-dioneand ethoxyethyl chloroformate as starting materials, the course of theprocess according to the invention can be represented by the followingequation:

[0344] Using, according to process (F),3-[4-(5-methyl-2-(4-fluoro-phenyl))-thiazolyl]-4-hydroxy-5,5-dimethyl-Δ³-dihydrofuran-2-oneand methyl chloromonothioformate as starting materials, the course ofthe reaction can be represented as follows:

[0345] Using, according to process (G),3-[4-(5-methyl-3-(4-methyl-phenyl))-thiazolyl]-5,5-pentamethylene-pyrrolidine-2,4-dioneand methanesulphonyl chloride as starting materials, the course of thereaction can be represented by the following equation:

[0346] Using, according to process (H),3-[4-(5-methyl-2-phenyl)-thiazolyl]-4-hydroxy-5,5-dimethyl-Δ³-dihydrofuran-2-oneand 2,2,2-trifluoroethyl methanethio-phosphonyl chloride as startingmaterials, the course of the reaction can be represented by thefollowing equation:

[0347] Using, according to process (I),3-[4-(5-methyl-2-(4-trifluoromethyl-phenyl))-thiazolyl]-5-cyclopropyl-5-methyl-pyrrolidine-2,4-dioneand NaOH as components, the course of the process according to theinvention can be represented by the following equation:

[0348] Using, according to process (Jα),3-[4-(5-methyl-2-(3-trifluoromethyl-phenyl))-thiazolyl]-4-hydroxy-5-tetramethylene-Δ³-dihydro-furan-2-oneand ethyl isocyanate as starting materials, the course of the reactioncan be represented by the following equation:

[0349] Using, according to process (Jβ),3-[4-(5-methyl-2-phenyl)-thiazolyl]-5-methyl-pyrrolidine-2,4-dione anddimethylcarbamoyl chloride as starting materials, the course of thereaction can be represented by the following scheme:

[0350] The compounds of the formula (II)

[0351] in which

[0352] A, B, D, Het and R⁸ are each as defined above

[0353] required as starting materials in the process (a) according tothe invention are novel.

[0354] The acylamino acid esters of the formula (II) are obtained, forexample, when amino acid derivatives of the formula (XV)

[0355] in which

[0356] A, B, R⁸ and D are each as defined above

[0357] are acylated with substituted hetarylacetic acid derivatives ofthe formula (XVI)

[0358] in which

[0359] Het is as defined above and

[0360] W represents a leaving group introduced by reagents foractivating carboxylic acids, such as carbonyldiimidazole,carbonyldiimides (such as, for example, dicyclohexylcarbodiimide),phosphorylating agents (such as, for example, POCl₃, BOP—Cl),halogenating agents, for example thionyl chloride, oxalyl chloride,phosgene or chloroformic esters

[0361] (Chem. Reviews 52, 237-416 (1953); Bhattacharya, Indian J. Chem.6, 341-5, 1968)

[0362] or when acylamino acids of the formula (XVII)

[0363] in which

[0364] A, B, D and Het are each as defined above

[0365] are esterified (Chem. Ind. (London) 1568 (1968)).

[0366] The compounds of the formula (XVII)

[0367] in which

[0368] A, B, D and Het are each as defined above

[0369] are novel.

[0370] The compounds of the formula (XVII) are obtained when amino acidsof the formula (XVIII)

[0371] in which

[0372] A, B and D are each as defined above

[0373] are acylated with substituted hetarylacetic acid derivatives ofthe formula (XVI)

[0374] in which

[0375] W and Het are each as defined above,

[0376] for example according to Schotten-Baumann (Organikum, VEBDeutscher Verlag der Wissenschaften, Berlin 1977, p. 505).

[0377] Some of the compounds of the formula (XVI) are novel. They can beprepared by processes known in principle (see, for example, H. Henecka,Houben-Weyl, Methoden der Organischen Chemie [Methods of OrganicChemistry], vol. 8, pp. 467-469 (1952)).

[0378] The compounds of the formula (XVI) are obtained, for example, byreacting substituted hetarylacetic acids of the formula (XIX)

[0379] in which

[0380] X and Y are each as defined above

[0381] with halogenating agents (for example thionyl chloride, thionylbromide, oxalyl chloride, phosgene, phosphorous trichloride, phosphoroustribromide or phosphorous pentachloride), if appropriate in the presenceof a diluent (for example optionally chlorinated aliphatic or aromatichydrocarbons, such as toluene or methylene chloride) at temperatures offrom −20° C. to 150° C., preferably from −10° C. to 100° C.

[0382] Some of the hetarylacetic acids of the formula (XIX) arecommercially available, some are known, or they can be prepared byprocesses known in principle

[0383] a) thiazolylacetic acids: C. S. Rooney et al. J. Med. Chem. 26,700-714 (1983); EP-A-368 592; M. S. Malamas et al. J. Med. Chem. 39,237-246 (1996); J. L. Collins et al. J. Med. Chem. 41, 5037-5054 (1998);NL-A-66 14 130;

[0384] b) Oxazolylacetic acids: K. Meguro et al., Chem. Pharm. Bull, 34,2840-2851 (1986), M. Sehi et al., Chem. Pharm. Bull. 36, 4435-4440(1988), Malmas et al., J. Med. Chem. 39, 237-245 (1996), EP 0 177 353A2, WO 87/03 807, WO 95/18 125, B. Hulin, J. Med. Chem. 35, 1853-1864(1992), EP 0 389 699 A 1.

[0385] Some of the compounds of the formulae (XV) and (XVIII) arecommercially available and/or are known and/or they can be prepared byknown processes (see, for example, Compagnon, Miocque Ann. Chim. (Paris)[14] 5, pp. 11-22, 23-27 (1970)).

[0386] The substituted cyclic aminocarboxylic acids of the formula(XVIIIa), in which A and B form a ring are generally obtainable by theBucherer-Bergs synthesis or by the Strecker synthesis, where they are ineach case obtained in different isomeric forms. Thus, the conditions ofthe Bucherer-Bergs synthesis give mainly the isomers (hereinbelow forthe sake of simplicity referred to as β) in which the radicals R and thecarboxyl group are in equatorial positions, whereas the conditions ofthe Strecker synthesis give mainly the isomers (hereinbelow for the sakeof simplicity referred to as α) in which the amino group and theradicals R are in equatorial positions.

[0387] (L. Munday, J. Chem. Soc. 4372 (1961): J. T. Eward, C.Jitrangeri, Can. J. Chem. 53, 3339 (1975).

[0388] Furthermore, the starting materials of the formula (II)

[0389] in which

[0390] A, B, D, Het and R⁸ are each as defined above

[0391] used in the above process (A) can be prepared by reacting aminonitriles of the formula (XX)

[0392] in which

[0393] A, B and D are each as defined above

[0394] with substituted hetarylacetic acid derivatives of the formula(XVI)

[0395] in which

[0396] W and Het are each as defined above

[0397] to give compounds of the formula (XXI)

[0398] in which

[0399] A, B, D and Het are each as defined above

[0400] which are subsequently subjected to an acidic alcoholysis.

[0401] The compounds of the formula (XXI) are likewise novel.

[0402] The compounds of the formula (III)

[0403] in which

[0404] A, B, Het and R⁸ are each as defined above

[0405] required as starting materials in the process (B) according tothe invention are novel.

[0406] They can be prepared by methods known in principle.

[0407] Thus, the compounds of the formula (III) are obtained, forexample, when 2-hydroxycarboxylic esters of the formula (XXII)

[0408] in which

[0409] A, B and R⁸ are each as defined above

[0410] are acylated with substituted hetarylacetic acid derivatives ofthe formula (XVI)

[0411] in which

[0412] W and Het are each as defined above

[0413] (Chem. Reviews 52, 237-416 (1953).

[0414] Furthermore, compounds of the formula (M) are obtained when

[0415] substituted hetarylacetic acids of the formula (XIX)

[0416] in which

[0417] Het is as defined above

[0418] are alkylated with α-halogenocarboxylic esters of the formula(XXIII)

[0419] in which

[0420] A, B and R⁸ are each as defined above and

[0421] Hal represents chlorine or bromine.

[0422] The compounds of the formula (IV)

[0423] in which

[0424] A, B, W¹, Het and R⁸ are each as defined above and

[0425] W¹ represents hydrogen, halogen, alkyl (preferably C₁-C₆-alkyl)or alkoxy (preferably C₁-C₆-alkoxy)

[0426] required as starting materials in the above process (C) arenovel.

[0427] They can be prepared by methods known in principle.

[0428] The compounds of the formula (IV) are obtained, for example, whencompounds of the formula (XXIV)

[0429] in which

[0430] Het and R⁸ are each as defined above

[0431] are acylated with 2-benzylthio-carbonyl halides of the formula(XXV)

[0432] in which

[0433] A, B and W¹ are each as defined above and

[0434] Hal represents halogen (in particular chlorine or bromine)

[0435] in the presence of strong bases (see, for example, M. S.Chambers, E. J. Thomas, D. J. Williams, J. Chem. Soc. Chem. Commun.,(1987), 1228).

[0436] Some of the compounds of the formula (XXIV) are commerciallyavailable, some are known, or they can be prepared by known processes:

[0437] a) thiazolyl acetic esters: C. S. Rooney et al., J. Med. Chem.26, 700-714 (1983), EP-A-368 592), M. S. Malmas et al., J. Med. Chem.39, 237-246 (1996); J. C. Collins et al., J. Med. Chem. 41, 5037-5054(1998); NL-A-6 614 130.

[0438] b) oxazolyl acetic acids: K. Meguro et al., Chem. Pharm. Bull,34, 2840-2851 (1986), M. Sehi et al., Chem. Pharm. Bull. 36, 4435-4440(1988), Malmas et al., J. Med. Chem. 39, 237-245 (1996), EP 0 177 353A2, WO 87/03 807, WO 95/18 125, B. Hulin, J. Med. Chem. 35, 1853-1864(1992), EP 0 389 699 A 1.

[0439] The acyl halides of the formula (V), carboxylic anhydrides of theformula (VI), chloroformic esters or chloroformic thioesters of theformula (VII), chloromonothioformic esters or chlorodithioformic estersof the formula (VIII), sulphonyl chlorides of the formula (IX),phosphorus compounds of the formula (X) and metal hydroxides, metalalkoxides or amines of the formulae (XI) and (XII) and isocyanates ofthe formula (XIII) and carbamoyl chlorides of the formula (XIV)furthermore required as starting materials for carrying out theprocesses (D), (E), (F), (G), (H), (I) and (J) according to theinvention are generally known compounds of organic or inorganicchemistry.

[0440] Some of the compounds of the formulae (XV), (XVIII), (XX),(XXII), (XXIII) and (XXV) are commercially available, some are known,and/or they can be prepared by methods known in principle.

[0441] The process (A) is characterized in that compounds of the formula(II) in which A, B, D, Het and R⁸ are each as defined above aresubjected to an intramolecular condensation in the presence of a base.

[0442] Suitable diluents for the process (A) according to the inventionare all inert organic solvents. Preference is given to usinghydrocarbons, such as toluene and xylene, furthermore ethers, such asdibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether anddiglycol dimethyl ether, moreover polar solvents, such as dimethylsulphoxide, sulpholane, dimethyl formamide and N-methylpyrrolidone, andalso alcohols, such as methanol, ethanol, propanol, iso-propanol,butanol, iso-butanol and tert-butanol.

[0443] Suitable bases (deprotonating agents) for carrying out theprocess (A) according to the invention are all customary protonacceptors. Preference is given to using alkali metal and alkaline earthmetal oxides, hydroxides and carbonates, such as sodium hydroxide,potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate,potassium carbonate and calcium carbonate, which can also be employed inthe presence of phase-transfer catalysts, such as, for example,triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464(=methyltrialkyl(C₈-C₁₀)ammonium chloride) or TDA 1(=tris-(methoxyethoxyethyl)-amine). Alkali metals such as sodium andpotassium can also be used. Furthermore, alkali metal and alkaline earthmetal halides and hydrides, such as sodium amide, sodium hydride andcalcium hydride, and additionally also alkali metal alkoxides, such assodium methoxide, sodium ethoxide and potassium tert-butoxide can beemployed.

[0444] When carrying out the process (A) according to the invention, thereaction temperatures can be varied within a relatively wide range. Ingeneral, the reaction is carried out at temperatures between −80° C. and180° C., preferably between −50° C. and 120° C.

[0445] The process (A) according to the invention is generally carriedout under atmospheric pressure.

[0446] When carrying out the process (A) according to the invention, thereaction components of the formula (II) and the deprotonating bases aregenerally employed in approximately double-equimolar amounts. However,it is also possible to use a relatively large excess (up to 3 mol) ofone component or the other.

[0447] The process (B) is characterized in that compounds of the formula(III) in which A, B, Het and R⁸ are each as defined above are subjectedto an intramolecular condensation in the presence of a diluent and inthe presence of a base.

[0448] Suitable diluents for the process (B) according to the inventionare all inert organic solvents. Preference is given to usinghydrocarbons, such as toluene and xylene, furthermore ethers such asdibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether anddiglycol dimethyl ether, moreover polar solvents, such as dimethylsulphoxide, sulpholane, dimethyl formamide and N-methylpyrrolidone, andalso alcohols, such as methanol, ethanol, propanol, iso-propanol,butanol, iso-butanol and tert-butanol.

[0449] Suitable bases (deprotonating agents) for carrying out theprocess (B) according to the invention are all customary protonacceptors. Preference is given to using alkali metal and alkaline earthmetal oxides, hydroxides and carbonates, such as sodium hydroxide,potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate,potassium carbonate and calcium carbonate, which can also be employed inthe presence of phase-transfer catalysts, such as, for example,triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464(=methyltrialkyl(C₈-C₁₀)ammonium chloride) or TDA 1(=tris-(methoxyethoxyethyl)-amine). Alkali metals such as sodium andpotassium can also be used. Furthermore, alkali metal and alkaline earthmetal amides and hydrides, such as sodium amide, sodium hydride andcalcium hydride, and additionally also alkali metal alkoxides, such assodium methoxide, sodium ethoxide and potassium tert-butoxide can beemployed.

[0450] When carrying out the process (B) according to the invention, thereaction temperatures can be varied within a relatively wide range. Ingeneral, the reaction is carried out at temperatures between −80° C. and180° C., preferably between −50° C. and 120° C.

[0451] The process (B) according to the invention is generally carriedout under atmospheric pressure.

[0452] When carrying out the process (B) according to the invention, thereaction components of the formula (III) and the deprotonating bases aregenerally employed in approximately equimolar amounts. However, it isalso possible to use a relatively large excess (up to 3 mol) of onecomponent or the other.

[0453] The process (C) is characterized in that compounds of the formula(IV) in which A, B, Het and R⁸ are each as defined above are cyclizedintramolecularly in the presence of an acid and, if appropriate, in thepresence of a diluent.

[0454] Suitable diluents for the process (C) according to the inventionare all inert organic solvents. Preference is given to usinghydrocarbons, such as toluene and xylene, furthermore halogenatedhydrocarbons, such as dichloromethane, chloroform, ethylene chloride,chlorobenzene, dichlorobenzene, moreover polar solvents, such asdimethyl sulphoxide, sulpholane, dimethylformamide andN-methyl-pyrrolidone. Furthermore, it is possible to employ alcoholssuch as methanol, ethanol, propanol, iso-propanol, butanol, isobutanol,tert-butanol.

[0455] If appropriate, the acid used can also serve as diluent.

[0456] Suitable acids for the process (C) according to the invention areall customary inorganic and organic acids, such as, for example,hydrohalic acids, sulphuric acid, alkyl-, aryl- and haloalkylsulphonicacids, in particular halogenated alkylcarboxylic acids, such as, forexample, trifluoroacetic acid.

[0457] When carrying out the process (C) according to the invention, thereaction temperatures can be varied within a relatively wide range. Ingeneral, the reaction is carried out at temperatures between −30° C. and250° C., preferably between 0° C. and 150° C.

[0458] The process (C) according to the invention is generally carriedout under atmospheric pressure.

[0459] When carrying out the process (C) according to the invention, thereaction components of the formula (IV) and the acid are employed, forexample, in equimolar amounts. However, it is also possible, ifappropriate, to use the acid as solvent or as catalyst.

[0460] The process (D-α) is characterized in that compounds of theformulae (I-1-A-a) to (I-3-B-a) are in each case reacted with carbonylhalides of the formula (V), if appropriate in the presence of a diluentand if appropriate in the presence of an acid binder.

[0461] Suitable diluents for the process (D-α) according to theinvention are all solvents which are inert towards the acyl halides.Preference is given to using hydrocarbons such as benzine, benzene,toluene, xylene and tetraline, furthermore halogenated hydrocarbons,such as methylene chloride, chloroform, carbon tetrachloride,chlorobenzene and o-dichlorobenzene, moreover ketones, such as acetoneand methyl isopropyl ketone, furthermore ethers, such as diethyl ether,tetrahydrofuran and dioxane, additionally carboxylic esters, such asethyl acetate, nitriles, such as acetonitrile, and also strongly polarsolvents, such as dimethylformamide, dimethylacetamide, dimethylsulphoxide and sulpholane. The hydrolytic stability of the acyl halidepermitting, the reaction can also be carried out in the presence ofwater.

[0462] Suitable acid binders for the reaction according to the process(D-α) according to the invention are all customary acid acceptors.Preference is given to using tertiary amines, such as triethylamine,pyridine, diazabicyclooctane (DABCO), diazabicycloundecene (DBU),diazabicyclononene (DBN), Hünig base and N,N-dimethyl-aniline,furthermore alkaline earth metal oxides, such as magnesium oxide andcalcium oxide, moreover alkali metal and alkaline earth metalcarbonates, such as sodium carbonate, potassium carbonate and calciumcarbonate, and also alkali metal hydroxides, such as sodium hydroxideand potassium hydroxide.

[0463] The reaction temperatures in the process (D-α) according to theinvention can be varied within a relatively wide range. In general, thereaction is carried out at temperatures between −20° C. and +150° C.,preferably between 0° C. and 100° C.

[0464] When carrying out the process (D-α) according to the invention,the starting materials of the formulae (I-1-A-a) to (1-3-B-a) and thecarbonyl halide of the formula (V) are generally in each case employedin approximately equivalent amounts. However, it is also possible toemploy a relatively large excess (up to 5 mol) of the carbonyl halide.Work-up is carried out by customary methods.

[0465] The process (D-β) is characterized in that compounds of theformulae (I-1-A-a) to (I-3-B-a) are reacted with carboxylic anhydridesof the formula (VI), if appropriate in the presence of a diluent and ifappropriate in the presence of an acid binder.

[0466] Preferred diluents for the process (D-β) according to theinvention are those diluents which are also preferred when acyl halidesare used. Otherwise, it is also possible for a carboxylic anhydrideemployed in excess to act simultaneously as diluent.

[0467] In the process (D-β), acid binders which are added, ifappropriate, are preferably those acid binders which are also preferredwhen acyl halides are used.

[0468] In the process (D-β) according to the invention, the reactiontemperatures can be varied within a relatively wide range. In general,the reaction is carried out at temperatures between −20° C. and +150°C., preferably between 0° C. and 100° C.

[0469] When carrying out the process (D-β) according to the invention,the starting materials of the formulae (I-1-A-a) to (I-3-B-a) and thecarboxylic anhydride of the formula (VI) are generally each employed inapproximately equivalent amounts. However, it is also possible to use arelatively large excess (up to 5 mol) of the carboxylic anhydride.Work-up is carried out by customary methods.

[0470] In general, the adopted procedure is to remove diluent and excesscarboxylic anhydride and also the carboxylic acid formed by distillationor by washing with an organic solvent or with water.

[0471] The process (E) is characterized in that compounds of theformulae (I-1-A-a) to (I-3-B-a) are in each case reacted withchloroformic esters or chloroformic thioesters of the formula (VII), ifappropriate in the presence of a diluent and if appropriate in thepresence of an acid binder.

[0472] Suitable acid binders for the reaction according to process (E)according to the invention are all customary acid acceptors. Preferenceis given to using tertiary amines, such as triethylamine, pyridine,DABCO, DBU, DBA, Hünig base and N,N-dimethyl-aniline, furthermorealkaline earth metal oxides, such as magnesium oxide and calcium oxide,moreover alkali metal carbonates and alkaline earth metal carbonates,such as sodium carbonate, potassium carbonate and calcium carbonate, andalso alkali metal hydroxides, such as sodium hydroxide and potassiumhydroxide.

[0473] Suitable diluents for the process (E) according to the inventionare all solvents which are inert towards the chloroformic esters orchloroformic thioesters. Preference is given to using hydrocarbons, suchas benzine, benzene, toluene, xylene and tetraline, furthermorehalogenated hydrocarbons, such as methylene chloride, chloroform, carbontetrachloride, chlorobenzene and o-dichlorobenzene, moreover ketones,such as acetone and methyl isopropyl ketone, furthermore ethers, such asdiethyl ether, tetrahydrofuran and dioxane, additionally carboxylicesters, such as ethyl acetate, nitriles, such as acetonitrile, and alsostrongly polar solvents, such as dimethylformamide, dimethylacetamide,dimethyl sulphoxide and sulpholane.

[0474] When carrying out the process (E) according to the invention, thereaction temperatures can be varied within a relatively wide range. Ifthe reaction is carried out in the presence of a diluent and an acidbinder, the reaction temperatures are generally between −20° C. and+100° C., preferably between 0° C. and 50° C.

[0475] The process (E) according to the invention is generally carriedout under atmospheric pressure.

[0476] When carrying out the process (E) according to the invention, thestarting materials of the formulae (I-1-A-a) to (I-3-B-a) and theappropriate chloroformic ester or chloroformic thioester of the formula(VII) are generally in each case employed in approximately equivalentamounts. However, it is also possible to employ a relatively largeexcess (up to 2 mol) of one component or the other. Work-up is carriedout by customary methods. In general, precipitated salts are removed andthe reaction mixture that remains is concentrated by stripping thediluent.

[0477] The process (F) according to the invention is characterized inthat compounds of the formulae (I-1-A-a) to (I-3-B-a) are in each casereacted with compounds of the formula (VIII) in the presence of adiluent and, if appropriate, in the presence of an acid binder.

[0478] In the preparation process (F), approximately 1 mole ofchloromonothioformic ester or chlorodithioformic ester of the formula(VIII) is reacted per mole of starting material of the formulae(I-1-A-a) to (I-3-B-a), at from 0 to 120° C., preferably from 20 to 60°C.

[0479] Suitable diluents which are added, if appropriate, are all inertpolar organic solvents, such as nitriles, esters, ethers, amides,sulphones, sulphoxides, but also halo-enoalkanes.

[0480] Preference is given to using acetonitrile, ethyl acetate,dimethylsulphoxide, tetrahydrofuran, dimethylformamide or methylenechloride.

[0481] If, in a preferred embodiment, the enolate salt of the compounds(I-1-A-a) to (I-3-B-a) is prepared by addition of strong deprotonatingagents, such as, for example, sodium hydride or potassium tert-butoxide,it is not necessary to add further acid binders.

[0482] If acid binders are employed, these are customary inorganic ororganic bases, for example sodium hydroxide, sodium carbonate, potassiumcarbonate, pyridine, triethylamine.

[0483] The reaction can be carried out at atmospheric pressure or underelevated pressure and is preferably carried out at atmospheric pressure.Work-up is carried out by customary methods.

[0484] The process (G) according to the invention is characterized inthat compounds of the formulae (I-1-A-a) to (I-3-B-a) are in each casereacted with sulphonyl chlorides of the formula (IX), if appropriate inthe presence of a diluent and if appropriate in the presence of an acidbinder.

[0485] In the preparation process (G), approximately 1 mole of sulphonylchloride of the formula (IX) is reacted per mole of starting material ofthe formulae (I-1-A-a) to (I-3-B-a) at from −20 to 150° C., preferablyat from 20 to 70° C.

[0486] Suitable diluents which are added if appropriate are all inertpolar organic solvents, such as nitriles, esters, ethers, amides,sulphones, sulphoxides or halogenated hydrocarbons, such as methylenechloride.

[0487] Preference is given to using acetonitrile, ethyl acetate,dimethyl sulphoxide, tetrahydrofuran, dimethylformamide, methylenechloride.

[0488] If, in a preferred embodiment, the enolate salt of the compounds(I-1-A-a) to (I-3-B-a) is prepared by addition of strong deprotonatingagents (such as, for example, sodium hydride or potassiumtert-butoxide), it is not necessary to add further acid binders.

[0489] If acid binders are employed, these are customary inorganic ororganic bases, for example sodium hydroxide, sodium carbonate, potassiumcarbonate, pyridine, triethylamine.

[0490] The reaction can be carried out at atmospheric pressure or underelevated pressure and is preferably carried out at atmospheric pressure.Work-up is carried out by customary methods.

[0491] The process (H) according to the invention is characterized inthat compounds of the formulae (I-1-A-a) to (I-3-B-a) are in each casereacted with phosphorus compounds of the formula (X), if appropriate inthe presence of a diluent and if appropriate in the presence of an acidbinder.

[0492] In the preparation process (H), 1 to 2, preferably 1 to 1.3, molof the phosphorus compound of the formula (X) are reacted per mole ofthe compounds (I-1-A-a) to (I-3-B-a), at temperatures between −40° C.and 150° C., preferably between −10 and 110° C., to give compounds ofthe formulae (I-1-A-e) to (I-3-B-e).

[0493] Suitable solvents which are added, if appropriate, are all inertpolar organic solvents, such as ethers, amides, nitrites, alcohols,sulphides, sulphones, sulphoxides, etc.

[0494] Preference is given to using acetonitrile, dimethyl sulphoxide,tetrahydrofuran, dimethylformamide, methylene chloride.

[0495] Suitable acid binders which are added, if appropriate, arecustomary inorganic or organic bases, such as hydroxides, carbonates oramines. Examples include sodium hydroxide, sodium carbonate, potassiumcarbonate, pyridine, triethylamine.

[0496] The reaction can be carried out at atmospheric pressure or underelevated pressure and is preferably carried out at atmospheric pressure.Work-up is carried out by customary methods of organic chemistry. Theresulting end products are preferably purified by crystallization,chromatographic purification or by so-called “incipient distillation”,i.e. removal of the volatile components under reduced pressure.

[0497] The process (I) is characterized in that compounds of theformulae (I-1-A-a) to (I-3-B-a) are reacted with metal hydroxides ormetal alkoxides of the formula (XI) or amines of the formula (XII), ifappropriate in the presence of a diluent.

[0498] Preferred diluents for the process (I) according to the inventionare ethers, such as tetrahydrofuran, dioxane, diethyl ether, or elsealcohols, such as methanol, ethanol, isopropanol, but also water.

[0499] The process (I) according to the invention is generally carriedout under atmospheric pressure.

[0500] The reaction temperatures are generally between −20° C. and 100°C., preferably between 0° C. and 50° C.

[0501] The process (J) according to the invention is characterized inthat compounds of the formulae (I-1-A-a) to (I-3-B-a) are in each casereacted (J-α) with compounds of the formula (XIII), if appropriate inthe presence of a diluent and if appropriate in the presence of acatalyst, or (J-β) with compounds of the formula (XIV), if appropriatein the presence of a diluent and if appropriate in the presence of anacid binder.

[0502] In the preparation process (J-α), approximately 1 mole ofisocyanate of the formula (XIII) is reacted per mole of startingmaterial of the formulae (I-1-A-a) to (I-3-B-a), at from 0 to 100° C.,preferably at from 20 to 50° C.

[0503] Suitable diluents which are added, if appropriate, are all inertorganic solvents, such as ethers, amides, nitriles, sulphones,sulphoxides.

[0504] If appropriate, catalysts may be added to accelerate thereaction. Very advantageously, the catalysts which are employed areorganotin compounds, such as, for example, dibutyltin dilaurate. Thereaction is preferably carried out at atmospheric pressure.

[0505] In the preparation process (J-β), approximately 1 mole ofcarbamoyl chloride of the formula (XIV) is reacted per mole of startingmaterial of the formulae (I-1-A-a) to (I-3-B-a), at from −20 to 150° C.,preferably from 0 to 70° C.z

[0506] Suitable diluents which are added, if appropriate, are all inertpolar organic solvents, such as nitriles, esters, ethers, amides,sulphones, sulphoxides or halogenated hydrocarbons.

[0507] Preference is given to using acetonitrile, ethyl acetate,dimethyl sulphoxide, tetrahydrofuran, dimethylformamide or methylenechloride.

[0508] If, in a preferred embodiment, the enolate salt of the compounds(I-1-A-a) to (I-3-B-a) is prepared by addition of strong deprotonatingagents (such as, for example, sodium hydride or potassiumtert-butoxide), it is not necessary to add further acid binders.

[0509] If acid binders are employed, these are customary inorganic ororganic bases, for example sodium hydroxide, sodium carbonate, potassiumcarbonate, triethylamine or pyridine.

[0510] The reaction can be carried out at atmospheric pressure or underelevated pressure and is preferably carried out at atmospheric pressure.Work-up is carried out by customary methods.

[0511] The active compounds are suitable for controlling animal pests,in particular insects, arachnids and nematodes, which are encountered inagriculture, in forestry, in the protection of stored products and ofmaterials, and in the hygiene sector, and have good plant tolerance andfavourable toxicity to warm-blooded animals. They may be preferablyemployed as plant protection agents. They are active against normallysensitive and resistant species and against all or some stages ofdevelopment. The abovementioned pests include:

[0512] From the order of the Isopoda, for example, Oniscus asellus,Armadillidium vulgare and Porcellio scaber.

[0513] From the order of the Diplopoda, for example, Blaniulusguttulatus.

[0514] From the order of the Chilopoda, for example, Geophiluscarpophagus and Scutigera spp.

[0515] From the order of the Symphyla, for example, Scutigerellaimmaculata.

[0516] From the order of the Thysanura, for example, Lepisma saccharina.

[0517] From the order of the Collembola, for example, Onychiurusarmatus.

[0518] From the order of the Orthoptera, for example, Acheta domesticus,Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp. andSchistocerca gregaria.

[0519] From the order of the Blattaria, for example, Blatta orientalis,Periplaneta americana, Leucophaea maderae, Blattella germanica.

[0520] From the order of the Dermaptera, for example, Forficulaauricularia.

[0521] From the order of the Isoptera, for example, Reticulitermes spp.

[0522] From the order of the Phthiraptera, for example, Pediculushumanus corporis, Haematopinus spp., Linognathus spp., Trichodectes spp.and Damalinia spp.

[0523] From the order of the Thysanoptera, for example, Hercinothripsfemoralis, Thrips tabaci, Thrips palmi and Frankliniella accidentalis.

[0524] From the order of the Heteroptera, for example, Eurygaster spp.,Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodniusprolixus and Triatoma spp.

[0525] From the order of the Homoptera, for example, Aleurodesbrassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii,Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi,Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix,Pemphigus spp., Macrosiphum avenae, Myzus spp., Phorodon humuli,Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettixcincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus,Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae,Pseudococcus spp. and Psylla spp.

[0526] From the order of the Lepidoptera, for example, Pectinophoragossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletisblancardella, Hyponomeuta padella, Plutella xylostella, Malacosomaneustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrixthurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltiaspp., Earias insulana, Heliothis spp., Mamestra brassicae, Panolisflammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pierisspp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleriamellonella, Tineola bisselliella, Tinea pellionella, Hofmannophilapseudospretella, Cacoecia podana, Capua reticulana, Choristoneurafumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana,Cnaphalocerus spp., Oulema oryzae.

[0527] From the order of the Coleoptera, for example, Anobium punctatum,Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus,Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedoncochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachnavarivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp.,Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus,Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogodermaspp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus,Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp.,Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha,Amphimallon soistitialis, Costelytra zealandica and Lissorhoptrusoryzophilus.

[0528] From the order of the Hymenoptera, for example, Diprion spp.,Hoplocampa spp., Lasius spp., Monomorium pharaonis and Vespa spp.

[0529] From the order of the Diptera, for example, Aedes spp., Anophelesspp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp.,Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebraspp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp.,Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinellafrit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae,Tipula paludosa, Hylemyia spp. and Liriomyza spp.

[0530] From the order of the Siphonaptera, for example, Xenopsyllacheopis and Ceratophyllus spp.

[0531] From the class of the Arachnida, for example, Scorpio maurus,Latrodectus mactans, Acarus siro, Argas spp., Omithodoros spp.,Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora,Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp.,Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemusspp., Bryobia praetiosa, Panonychus spp., Tetranychus spp.,Hemitarsonemus spp., Brevipalpus spp.

[0532] The phytoparasitic nematodes include, for example, Pratylenchusspp., Radopholus similis, Ditylenchus dipsaci, Tylenchulussemipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp.,Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp.,Bursaphelenchus spp.

[0533] If appropriate, the compounds according to the invention can, atcertain concentrations or application rates, also be used as herbicidesor microbicides, for example as fungicides, antimycotics andbactericides. If appropriate, they can also be employed as intermediatesor precursors for the synthesis of other active compounds.

[0534] All plants and plant parts can be treated in accordance with theinvention. Plants are to be understood as meaning in the present contextall plants and plant populations such as desired and undesired wildplants or crop plants (including naturally occurring crop plants). Cropplants can be plants which can be obtained by conventional plantbreeding and optimization methods or by biotechnological and recombinantmethods or by combinations of these methods, including the transgenicplants and inclusive of the plant cultivars protectable or notprotectable by plant breeders' rights. Plant parts are to be understoodas meaning all parts and organs of plants above and below the ground,such as shoot, leaf, flower and root, examples which may be mentionedbeing leaves, needles, stalks, stems, flowers, fruit bodies, fruits,seeds, roots, tubers and rhizomes. The plant parts also includeharvested material, and vegetative and generative propagation material,for example cuttings, tubers, rhizomes, offsets and seeds.

[0535] Treatment according to the invention of the plants and plantparts with the active compounds is carried out directly or by allowingthe compounds to act on the surroundings, environment or storage spaceby the customary treatment methods, for example by immersion, spraying,evaporation, fogging, scattering, painting on and, in the case ofpropagation material, in particular in the case of seeds, also byapplying one or more coats.

[0536] As already mentioned above, it is possible to treat all plantsand their parts according to the invention. In a preferred embodiment,wild plant species and plant cultivars, or those obtained byconventional biological breeding, such as crossing or protoplast fusion,and parts thereof, are treated. In a further preferred embodiment,transgenic plants and plant cultivars obtained by genetical engineering,if appropriate in combination with conventional methods (GeneticallyModified Organisms), and parts thereof are treated. The term “parts” or“parts of plants” or “plant parts” has been explained above.

[0537] Particularly preferably, plants of the plant cultivars which arein each case commercially available or in use are treated according tothe invention.

[0538] Depending on the plant species or plant cultivars, their locationand growth conditions (soils, climate, vegetation period, diet), thetreatment according to the invention may also result in superadditive(“synergistic”) effects. Thus, for example, reduced application ratesand/or a widening of the activity spectrum and/or an increase in theactivity of the substances and compositions to be used according to theinvention, better plant growth, increased tolerance to high or lowtemperatures, increased tolerance to drought or to water or soil saltcontent, increased flowering performance, easier harvesting, acceleratedmaturation, higher harvest yields, better quality and/or a highernutritional value of the harvested products, better storage stabilityand/or processability of the harvested products are possible whichexceed the effects which were actually to be expected.

[0539] The transgenic plants or plant cultivars (i.e. those obtained bygenetical engineering) which are preferably to be treated according tothe invention include all plants which, in the genetic modification,received genetic material which imparted particularly advantageoususeful properties (“traits”) to these plants. Examples of suchproperties are better plant growth, increased tolerance to high or lowtemperatures, increased tolerance to drought or to water or soil saltcontent, increased flowering performance, easier harvesting, acceleratedmaturation, higher harvest yields, better quality and/or a highernutritional value of the harvested products, better storage stabilityand/or processability of the harvested products. Further andparticularly emphasized examples of such properties are a better defenceof the plants against animal and microbial pests, such as againstinsects, mites, phytopathogenic fungi, bacteria and/or viruses, and alsoincreased tolerance of the plants to certain herbicidally activecompounds. Examples of transgenic plants which may be mentioned are theimportant crop plants, such as cereals (wheat, rice), maize, soya beans,potatoes, cotton, oilseed rape and also fruit plants (with the fruitsapples, pears, citrus fruits and grapes), and particular emphasis isgiven to maize, soya beans, potatoes, cotton and oilseed rape. Traitsthat are emphasized are in particular increased defence of the plantsagainst insects by toxins formed in the plants, in particular thoseformed in the plants by the genetic material from Bacillus thuringiensis(for example by the genes CryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA,CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CryIF and also combinations thereof)(hereinbelow referred to as “Bt plants”). Traits that are furthermoreparticularly emphasized are the increased tolerance of the plants tocertain herbicidally active compounds, for example imidazolinones,sulphonylureas, glyphosate or phosphinotricin (for example the “PAT”gene). The genes which impart the desired traits in question can also bepresent in combination with one another in the transgenic plants.Examples of “Bt plants” which may be mentioned are maize varieties,cotton varieties, soya bean varieties and potato varieties which aresold under the trade names YIELD GARD® (for example maize, cotton, soyabeans), KnockOut® (for example maize), StarLink® (for example maize),Bollgard® (cotton), Nucotn® (cotton) and NewLeaf® (potato). Examples ofherbicide-tolerant plants which may be mentioned are maize varieties,cotton varieties and soya bean varieties which are sold under the tradenames Roundup Ready® (tolerance to glyphosate, for example maize,cotton, soya bean), Liberty Link® (tolerance to phosphinotricin, forexample oilseed rape), IMI® (tolerance to imidazolinones) and STS®(tolerance to sulphonylurea, for example maize). Herbicide-resistantplants (plants bred in a conventional manner for herbicide tolerance)which may be mentioned include the varieties sold under the nameClearfield® (for example maize). Of course, these statements also applyto plant cultivars having these genetic traits or genetic traits stillto be developed, which plants will be developed and/or marketed in thefuture.

[0540] The plants listed can be treated according to the invention in aparticularly advantageous manner with the compounds of the formula (I).The preferred ranges stated above for the active compounds also apply tothe treatment of these plants. Particular emphasis is given to thetreatment of plants with the mixtures specifically mentioned in thepresent text.

[0541] The active compounds can be converted to the customaryformulations, such as solutions, emulsions, wettable powders,suspensions, powders, dusts, pastes, soluble powders, granules,suspension-emulsion concentrates, natural and synthetic materialsimpregnated with active compound and microencapsulations in polymericsubstances.

[0542] These formulations are produced in a known manner, for example bymixing the active compounds with extenders, that is, liquid solvents,and/or solid carriers, optionally with the use of surfactants, that isemulsifiers and/or dispersants, and/or foam-formers.

[0543] If the extender used is water, it is also possible to employ forexample organic solvents as auxiliary solvents. Essentially, suitableliquid solvents are: aromatics such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics or chlorinated aliphatichydrocarbons such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons such as cyclohexane or paraffins, forexample petroleum fractions, mineral and vegetable oils, alcohols suchas butanol or glycol and also their ethers and esters, ketones such asacetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,strongly polar solvents such as dimethylformamide and dimethylsulphoxide, and also water.

[0544] As solid carriers there are suitable:

[0545] for example ammonium salts and ground natural minerals such askaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite ordiatomaceous earth, and ground synthetic minerals, such as highlydisperse silica, alumina and silicates; as solid carriers for granulesthere are suitable: for example crushed and fractionated natural rockssuch as calcite, marble, pumice, sepiolite and dolomite, and alsosynthetic granules of inorganic and organic meals, and granules oforganic material such as sawdust, coconut shells, maize cobs and tobaccostalks; as emulsifiers and/or foam-formers there are suitable:

[0546] for example nonionic and anionic emulsifiers, such aspolyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers,for example alkylaryl polyglycol ethers, alkylsulphonates, alkylsulphates, arylsulphonates and also protein hydrolysates; as dispersantsthere are suitable: for example lignin-sulphite waste liquors andmethylcellulose.

[0547] Tackifiers such as carboxymethylcellulose and natural andsynthetic polymers in the form of powders, granules or latices, such asgum arabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Other additives can bemineral and vegetable oils.

[0548] It is possible to use colorants such as inorganic pigments, forexample iron oxide, titanium oxide and Prussian Blue, and organicdyestuffs, such as alizarin dyestuffs, azo dyestuffs and metalphthalocyanine dyestuffs, and trace nutrients such as salts of iron,manganese, boron, copper, cobalt, molybdenum and zinc.

[0549] The formulations generally comprise between 0.1 and 95% by weightof active compound, preferably between 0.5 and 90%.

[0550] The active compound according to the invention can be present inits commercially available formulations and in the use forms, preparedfrom these formulations, as a mixture with other active compounds, suchas insecticides, attractants, sterilizing agents, bactericides,acaricides, nematicides, fungicides, growth-regulating substances orherbicides. The insecticides include, for example, phosphoric acidesters, carbamates, carboxylates, chlorinated hydrocarbons, phenylureasand substances produced by microorganisms, inter alia.

[0551] Particularly favourable examples of co-components in mixtures arethe following compounds:

[0552] Fungicides:

[0553] aldimorph, ampropylfos, ampropylfos-potassium, andoprim,anilazine, azaconazole, azoxystrobin,

[0554] benalaxyl, benodanil, benomyl, benzamacril, benzamacryl-isobutyl,bialaphos, binapacryl, biphenyl, bitertanol, blasticidin-S,bromuconazole, bupirimate, buthiobate,

[0555] calcium polysulphide, capsimycin, captafol, captan, carbendazim,carboxin, carvon, quinomethionate, chlobenthiazone, chlorfenazole,chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon,cufraneb, cymoxanil, cyproconazole, cyprodinil, cyprofuram,

[0556] debacarb, dichlorophen, diclobutrazole, diclofluanid,diclomezine, dicloran, diethofencarb, difenoconazole, dimethirimol,dimethomorph, diniconazole, diniconazole-M, dinocap, diphenylamine,dipyrithione, ditalimfos, dithianon, dodemorph, dodine, drazoxolon,

[0557] edifenphos, epoxiconazole, etaconazole, ethirimol, etridiazole,

[0558] famoxadon, fenapanil, fenarimol, fenbuconazole, fenfuram,fenitropan, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate,fentin hydroxide, ferbam, ferimzone, fluazinam, flumetover, fluoromide,fluquinconazole, flurprimidol, flusilazole, flusulfamide, flutolanil,flutriafol, folpet, fosetyl-aluminium, fosetyl-sodium, fthalide,fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole,furconazole-cis, furmecyclox,

[0559] guazatine,

[0560] hexachlorobenzene, hexaconazole, hymexazole,

[0561] imazalil, imibenconazole, iminoctadine, iminoctadine albesilate,iminoctadine triacetate, iodocarb, ipconazole, iprobenfos (IBP),iprodione, irumamycin, isoprothiolane, isovaledione,

[0562] kasugamycin, kresoxim-methyl, copper preparations, such as:copper hydroxide, copper naphthenate, copper oxychloride, coppersulphate, copper oxide, oxine-copper and Bordeaux mixture,

[0563] mancopper, mancozeb, maneb, meferimzone, mepanipyrim, mepronil,metalaxyl, metconazole, methasulfocarb, methfuroxam, metiram,metomeclam, metsulfovax, mildiomycin, myclobutanil, myclozolin,

[0564] nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol,

[0565] ofurace, oxadixyl, oxamocarb, oxolinic acid, oxycarboxim,oxyfenthiin,

[0566] paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen,pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz,procymidone, propamocarb, propanosine-sodium, propiconazole, propineb,pyrazophos, pyrifenox, pyrimethanil, pyroquilon, pyroxyfur,

[0567] quinconazole, quintozene (PCNB),

[0568] sulphur and sulphur preparations,

[0569] tebuconazole, tecloftalam, tecnazene, tetcyclasis, tetraconazole,thiabendazole, thicyofen, thifluzamide, thiophanate-methyl, thiram,tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol,triazbutil, triazoxide, trichlamide, tricyclazole, tridemorph,triflumizole, triforine, triticonazole,

[0570] uniconazole,

[0571] validamycin A, vinclozolin, viniconazole,

[0572] zarilamide, zineb, ziram and also

[0573] Dagger G,

[0574] OK-8705,

[0575] OK-8801,

[0576]α-(1,1-dimethylethyl)-β-(2-phenoxyethyl)-1H-1,2,4-triazole-1-ethanol,

[0577] α-(2,4-dichlorophenyl)-β-fluoro-β-propyl-1H-1,2,4-triazole-1-ethanol,

[0578]α-(2,4-dichlorophenyl)-β-methoxy-α-methyl-1H-1,2,4-triazole-1-ethanol,

[0579]α-(5-methyl-1,3-dioxan-5-yl)-β-[[4-(trifluoromethyl)-phenyl]-methylene]-1H-1,2,4-triazole-1-ethanol,

[0580](5RS,6RS)-6-hydroxy-2,2,7,7-tetramethyl-5-(1H-1,2,4-triazol-1-yl)-3-octanone,

[0581] (E)-α-(methoxyimino)-N-methyl-2-phenoxy-phenylacetamide,

[0582] 1 -isopropyl{2-methyl-1-[[[1-(4-methylphenyl)-ethyl]-amino]-carbonyl]-propyl}-carbamate,

[0583]1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-ethanone-O-(phenylmethyl)-oxime,

[0584] 1-(2-methyl-1-naphthalenyl)-1H-pyrrol-2,5-dione,

[0585] 1-(3,5-dichlorophenyl)-3-(2-propenyl)-2,5-pyrrolidindione,

[0586] 1-[(diiodomethyl)-sulphonyl]-4-methyl-benzene,

[0587]1-[[2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl]-methyl]-1H-imidazole,

[0588]1-[[2-(4-chlorophenyl)-3-phenyloxiranyl]-methyl]-1H-1,2,4-triazole,

[0589]1-[1-[2-[(2,4-dichlorophenyl)-methoxy]-phenyl]-ethenyl]-1H-imidazole,

[0590] 1-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinole,

[0591]2′,6′-dibromo-2-methyl-4′-trifluoromethoxy-4′-trifluoro-methyl-1,3-thiazole-5-carboxanilide,

[0592]2,2-dichloro-N-[1-(4-chlorophenyl)-ethyl]-1-ethyl-3-methyl-cyclopropanecarboxamide,

[0593] 2,6-dichloro-5-(methylthio)-4-pyrimidinyl-thiocyanate,

[0594] 2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide,

[0595] 2,6-dichloro-N-[[4-(trifluoromethyl )-phenyl]-methyl]-benzamide,

[0596] 2-(2,3,3-triiodo-2-propenyl)-2H-tetrazole,

[0597]2-[(1-methylethyl)-sulphonyl]-5-(trichloromethyl)-1,3,4-thiadiazole,

[0598]2-[[6-deoxy4-O-(4-O-methyl-β-D-glycopyranosyl)-α-D-glucopyranosyl]-amino]-4-methoxy-1H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile,

[0599] 2-aminobutane,

[0600] 2-bromo-2-(bromomethyl)-pentanedinitrile,

[0601] 2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-3-pyridinecarboxamide,

[0602]2-chloro-N-(2,6-dimethylphenyl)-N-(isothiocyanatomethyl)-acetamide,

[0603] 2-phenylphenol (OPP),

[0604] 3,4-dichloro-1-[4-(difluoromethoxy)-phenyl]-1H-pyrrol-2,5-dione,

[0605]3,5-dichloro-N-[cyano[(1-methyl-2-propynyl)-oxy]-methyl]-benzamide,

[0606] 3-(1,1-dimethylpropyl-1-oxo-1H-indene-2-carbonitrile,

[0607] 3-[2-(4-chlorophenyl)-5-ethoxy-3-isoxazolidinyl]-pyridine,

[0608]4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulphonamide,

[0609] 4-methyl-tetrazolo[1,5-a]quinazolin-5(4H)-one,

[0610] 8-(1,1-dimethylethyl)-N-ethyl-N-propyl-1,4-dioxaspiro[4.5]decane-2-methanamine,

[0611] 8-hydroxyquinoline sulphate,

[0612] 9H-xanthene-2-[(phenylamino)-carbonyl]-9-carboxylic hydrazide,

[0613]bis-(1-methylethyl)-3-methyl-4-[(3-methylbenzoyl)-oxy]-2,5-thiophenedicarboxylate,

[0614] cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-cycloheptanol,

[0615]cis-4-[3-[4-(1,1-dimethylpropyl)-phenyl-2-methylpropyl]-2,6-dimethyl-morpholinehydrochloride,

[0616] ethyl [(4-chlorophenyl)-azo]-cyanoacetate,

[0617] potassium bicarbonate,

[0618] methanetetrathiol-sodium salt,

[0619] methyl1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate,

[0620] methylN-(2,6-dimethylphenyl)-N-(5-isoxazolylcarbonyl)-DL-alaninate,

[0621] methyl N-(chloroacetyl)-N-(2,6-dimethylphenyl)-DL-alaninate,

[0622] N-(2,3-dichloro-4-hydroxyphenyl)-1-methyl-cyclohexanecarboxamide,

[0623]N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-furanyl)-acetamide,

[0624]N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-thienyl)-acetamide,

[0625] N-(2-chloro-4-nitrophenyl)-4-methyl-3-nitro-benzenesulphonamide,

[0626] N-(4-cyclohexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidinamine,

[0627] N-(4-hexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidinamine,

[0628]N-(5-chloro-2-methylphenyl)-2-methoxy-N-(2-oxo-3-oxazoldinyl)-acetamide,

[0629] N-(6-methoxy)-3-pyridinyl )-cyclopropanecarboxamide,

[0630] N-[2,2,2-trichloro-1-[(chloroacetyl)-amino]-ethyl]-benzamide,

[0631]N-[3-chloro-4,5-bis(2-propinyloxy)-phenyl]-N′-methoxy-methanimidamide,

[0632] N-formyl-N-hydroxy-DL-alanine-sodium salt,

[0633] O,O-diethyl[2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate,

[0634] O-methyl S-phenyl phenylpropylphosphoramidothioate,

[0635] S-methyl 1,2,3-benzothiadiazole-7-carbothioate,

[0636] spiro[2H]-1-benzopyrane-2,1′(3 ′H)-isobenzofuran]-3′-one,

[0637] Bactericides:

[0638] bronopol, dichlorophen, nitrapyrin, nickeldimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid,oxytetracyclin, probenazole, streptomycin, tecloftalam, copper sulphateand other copper preparations.

[0639] Insecticides/acaricides/nematicides:

[0640] abamectin, acephate, acetamiprid, acrinathrin, alanycarb,aldicarb, aldoxycarb, alpha-cypernethrin, alphamethrin, amitraz,avermectin, AZ 60541, azadirachtin, azamethiphos, azinphos A, azinphosM, azocyclotin,

[0641]Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis,Bacillus thuringiensis, baculoviruses, Beauveria bassiana, Beauveriatenella, bendiocarb, benfuracarb, bensultap, benzoximate,betacyfluthrin, bifenazate, bifenthrin, bioethanomethrin, biopermethrin,BPMC, bromophos A, bufencarb, buprofezin, butathiofos, butocarboxim,butylpyridaben,

[0642] cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan,cartap, chloethocarb, chlorethoxyfos, chlorfenapyr, chlorfenvinphos,chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M,chlovaporthrin, cis-resmethrin, cispermethrin, clocythrin, cloethocarb,clofentezine, cyanophos, cycloprene, cycloprothrin, cyfluthrin,cyhalothrin, cyhexatin, cypermethrin, cyromazine,

[0643] deltamethrin, demeton M, demeton S, demeton-S-methyl,diafenthiuron, diazinon, dichlorvos, diflubenzuron, dimethoate,dimethylvinphos, diofenolan, disulfoton, docusat-sodium, dofenapyn,

[0644] eflusilanate, emamectin, empenthrin, endosulfan, Entomopfthoraspp., esfenvalerate, ethiofencarb, ethion, ethoprophos, etofenprox,etoxazole, etrimfos,

[0645] fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion,fenothiocarb, fenoxacrim, fenoxycarb, fenpropathrin, fenpyrad,fenpyrithrin, fenpyroximate, fenvalerate, fipronil, fluazinam,fluazuron, flubrocythrinate, flucycloxuron, flucythrinate, flufenoxuron,flutenzine, fluvalinate, fonophos, fosmethilan, fosthiazate, fubfenprox,furathiocarb,

[0646] granulosis viruses,

[0647] halofenozide, HCH, heptenophos, hexaflumuron, hexythiazox,hydroprene,

[0648] imidacloprid, isazofos, isofenphos, isoxathion, ivermectin,

[0649] nuclear polyhedrosis viruses,

[0650] lambda-cyhalothrin, lufenuron,

[0651] malathion, mecarbam, metaldehyde, methamidophos, Metharhiziumanisopliae, Metharhizium flavoviride, methidathion, methiocarb,methomyl, methoxyfenozide, metolcarb, metoxadiazone, mevinphos,milbemectin, monocrotophos,

[0652] naled, nitenpyram, nithiazine, novaluron,

[0653] omethoate, oxamyl, oxydemethon M,

[0654]Paecilomyces fumosoroseus, parathion A, parathion M, permethrin,phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim,pirimicarb, pirimiphos A, pirimiphos M, profenofos, promecarb, propoxur,prothiofos, prothoate, pymetrozine, pyraclofos, pyresmethrin, pyrethrum,pyridaben, pyridathion, pyrimidifen, pyriproxyfen,

[0655] quinalphos,

[0656] ribavirin,

[0657] salithion, sebufos, silafluofen, spinosad, sulfotep, sulprofos,

[0658] tau-fluvalinate, tebufenozide, tebufenpyrad, tebupirimiphos,teflubenzuron, tefluthrin, temephos, temivinphos, terbufos,tetrachlorvinphos, theta-cypermethrin, thiamethoxam, thiapronil,thiatriphos, thiocyclam hydrogen oxalate, thiodicarb, thiofanox,thuringiensin, tralocythrin, tralomethrin, triarathene, triazamate,triazophos, triazuron, trichlophenidine, trichlorfon, triflumuron,trimethacarb,

[0659] vamidothion, vaniliprole, Verticillium lecanii,

[0660] YI 5302,

[0661] zeta-cypermethrin, zolaprofos,

[0662](1R-cis)-[5-(phenylmethyl)-3-furanyl]-methyl-3-[(dihydro-2-oxo-3(2H)-furanylidene)-methyl]-2,2-dimethylcyclopropanecarboxylate,

[0663](3-phenoxyphenyl)-methyl-2,2,3,3-tetramethylcyclopropanecarboxylate,

[0664]1-[(2-chloro-5-thiazolyl)methyl]tetrahydro-3,5-dimethyl-N-nitro-1,3,5-triazine-2(1H)-imine,

[0665] 2-(2-chloro-6-fluorophenyl)-4-[4-(1,1-dimethylethyl)phenyl]-4,5-dihydro-oxazole,

[0666] 2-(acetyloxy)-3-dodecyl-1,4-naphthalenedione,

[0667]2-chloro-N-[[[4-(1-phenylethoxy)-phenyl]-amino]-carbonyl]-benzamide,

[0668]2-chloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)-phenyl]-amino]-carbonyl]-benzamide,

[0669] 3-methylphenyl propylcarbamate.

[0670] 4-[4-(4-ethoxyphenyl)-4-methylpentyl]-1-fluoro-2-phenoxy-benzene,

[0671]4-chloro-2-(1,1-dimethylethyl)-5-[[2-(2,6-dimethyl-4-phenoxyphenoxy)ethyl]thio]-3(2H)-pyridazinone,

[0672]4-chloro-2-(2-chloro-2-methylpropyl)-5-[(6-iodo-3-pyridinyl)methoxy]-3(2H)-pyridazinone,

[0673]4-chloro-5-[(6-chloro-3-pyridinyl)methoxy]-2-(3,4-dichlorophenyl)-3(2H)-pyridazinone,

[0674]Bacillus thuringiensis strain EG-2348,

[0675] 2-benzoyl-1-(1,1-dimethylethyl)-hydrazinobenzoic acid,

[0676]2,2-dimethyl-3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-en-4-ylbutanoate,

[0677][3-[(6-chloro-3-pyridinyl)methyl]-2-thiazolidinylidene]-cyanamide,

[0678] dihydro-2-(nitromethylene)-2H-1,3-thiazine-3(4H)-carboxaldehyde,

[0679] ethyl [2-[[1,6-dihydro-6-oxo-1-(phenylmethyl)-4-pyridazinyl]oxy]ethyl]-carbamate,

[0680] N-(3,4,4-trifluoro- 1-oxo-3-butenyl)-glycine,

[0681]N-(4-chlorophenyl)-3-[4-(difluoromethoxy)phenyl]-4,5-dihydro-4-phenyl-1H-pyrazole-1-carboxamide,

[0682] N-[(2-chloro-5-thiazolyl)methyl]-N′-methyl-N″-nitro-guanidine,

[0683] N-methyl-N′-(1-methyl-2-propenyl)- 1,2-hydrazinedicarbothioamide,

[0684] N-methyl-N′-2-propenyl-1,2-hydrazinedicarbothioamide,

[0685]O,O-diethyl[2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate.

[0686] It is also possible to admix other known active compounds, suchas herbicides, fertilizers and growth regulators.

[0687] When used as insecticides, the active compounds according to theinvention can furthermore be present in their commercially availableformulations and in the use forms, prepared from these formulations, asa mixture with synergistic agents. Synergistic agents are compoundswhich increase the action of the active compounds, without it beingnecessary for the synergistic agent added to be active itself.

[0688] The active compound content of the use forms prepared from thecommercially available formulations can vary within wide limits. Theactive compound concentration of the use forms can be from 0.0000001 to95% by weight of active compound, preferably between 0.0001 and 1% byweight.

[0689] The compounds are employed in a customary manner appropriate forthe use forms.

[0690] When used against hygiene pests and pests of stored products, theactive compound is distinguished by an excellent residual action on woodand clay as well as a good stability to alkali on limed substrates.

[0691] The active compounds according to the invention act not onlyagainst plant, hygiene and stored product pests, but also in theveterinary medicine sector against animal parasites (ectoparasites),such as hard ticks, soft ticks, mange mites, leaf mites, flies (bitingand licking), parasitic fly larvae, lice, hair lice, feather lice andfleas. These parasites include:

[0692] From the order of the Anoplurida, for example, Haematopinus spp.,Linognathus spp., Pediculus spp., Phtirus spp. and Solenopotes spp.

[0693] From the order of the Mallophagida and the suborders Amblycerinaand Ischnocerina, for example, Trimenopon spp., Menopon spp., Trinotonspp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp.,Trichodectes spp. and Felicola spp.

[0694] From the order of the Diptera and the suborders Nematocerina andBrachycerina, for example, Aedes spp., Anopheles spp., Culex spp.,Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp.,Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanusspp., Haematopota spp., Philipomyla spp., Braula spp., Musca spp.,Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fanniaspp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp.,Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp.,Gasterophilus spp., Hippobosca spp., Lipoptena spp. and Melophagus spp.

[0695] From the order of the Siphonapterida, for example Pulex spp.,Ctenocephalides spp., Xenopsylla spp. and Ceratophyllus spp.

[0696] From the order of the Heteropterida, for example, Cimex spp.,Triatoma spp., Rhodnius spp. and Panstrongylus spp.

[0697] From the order of the Blattanrda, for example Blatta orientalis,Periplaneta americana, Blattela germanica and Supella spp.

[0698] From the subclass of the Acaria (Acarida) and the orders of theMeta- and Mesostigmata, for example, Argas spp., Ornithodorus spp.,Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentorspp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssusspp., Raillietia spp., Pneumonyssus spp., Sternostoma spp. and Varroaspp.

[0699] From the order of the Actinedida (Prostigmata) und Acaridida(Astigmata), for example, Acarapis spp., Cheyletiella spp.,Omithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp.,Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp.,Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp.,Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,Knemidocoptes spp., Cytodites spp. and Laminosioptes spp.

[0700] The active compounds of the formula (I) according to theinvention are also suitable for controlling arthropods which infestagricultural productive livestock, such as, for example, cattle, sheep,goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens,turkeys, ducks, geese and bees, other pets, such as, for example, dogs,cats, caged birds and aquarium fish, and also so-called test animals,such as, for example, hamsters, guinea pigs, rats and mice. Bycontrolling these arthropods, cases of death and reduction inproductivity (for meat, milk, wool, hides, eggs, honey etc.) should bediminished, so that more economic and easier animal husbandry ispossible by use of the active compounds according to the invention.

[0701] The active compounds according to the invention are used in theveterinary sector in a known manner by enteral administration in theform of, for example, tablets, capsules, potions, drenches, granules,pastes, boluses, the feed-through process and suppositories, byparenteral administration, such as, for example, by injection(intramuscular, subcutaneous, intravenous, intraperitoneal and thelike), implants by nasal administration, by dermal use in the form, forexample, of dipping or bathing, spraying, pouring on and spotting on,washing and powdering, and also with the aid of molded articlescontaining the active compound, such as collars, ear marks, tail marks,limb bands, halters, marking devices and the like.

[0702] When used for cattle, poultry, pets and the like, the activecompounds of the formula (1) can be used as formulations (for examplepowders, emulsions, free-flowing compositions), which comprise theactive compounds in an amount of 1 to 80% by weight, directly or after100 to 10 000-fold dilution, or they can be used as a chemical bath.

[0703] It has furthermore been found that the compounds of the formula(I) according to the invention also have a strong insecticidal actionagainst insects which destroy industrial materials.

[0704] The following insects may be mentioned as examples and aspreferred—but without a limitation:

[0705] Beetles, such as

[0706]Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum,Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex,Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus,Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylonaequale, Minthes rugicollis, Xyleborus spec. Tryptodendron spec. Apatemonachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylonspec. Dinoderus minutus.

[0707] Hymenopterons, such as

[0708]Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerusaugur.

[0709] Termites, such as

[0710]Kalotermes flavicollis, Cryptotermes brevis, Heterotermesindicola, Reticulitermes flavipes, Reticulitermes santonensis,Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsisnevadensis, Coptotermes formosanus. Bristletails, such as Lepismasaccarina.

[0711] Industrial materials in the present connection are to beunderstood as meaning non-living materials, such as, preferably,plastics, adhesives, sizes, papers and cards, leather, wood andprocessed wood products and coating compositions.

[0712] Wood and processed wood products are materials to be protected,especially preferably, from insect infestation.

[0713] Wood and processed wood products which can be protected by theagents according to the invention or mixtures comprising these are to beunderstood as meaning, for example: building timber, wooden beams,railway sleepers, bridge components, boat jetties, wooden vehicles,boxes, pallets, containers, telegraph poles, wood panelling, woodenwindows and doors, plywood, chipboard, joinery or wooden products whichare used quite generally in house-building or in building joinery.

[0714] The active compounds can be used as such, in the form ofconcentrates or in generally customary formulations, such as powders,granules, solutions, suspensions, emulsions or pastes.

[0715] The formulations mentioned can be prepared in a manner known perse, for example by mixing the active compounds with at least one solventor diluent, emulsifier, dispersing agent and/or binder or fixing agent,a water repellent, if appropriate siccatives and UV stabilizers and ifappropriate dyestuffs and pigments, and also other processingauxiliaries.

[0716] The insecticidal compositions or concentrates used for thepreservation of wood and wood-derived timber products comprise theactive compound according to the invention in a concentration of 0.0001to 95% by weight, in particular 0.001 to 60% by weight.

[0717] The amount of the compositions or concentrates employed dependson the nature and occurrence of the insects and on the medium. Theoptimum amount employed can be determined for the use in each case by aseries of tests. In general, however, it is sufficient to employ 0.0001to 20% by weight, preferably 0.001 to 10% by weight, of the activecompound, based on the material to be preserved.

[0718] Solvents and/or diluents which are used are an organic chemicalsolvent or solvent mixture and/or an oily or oil-like organic chemicalsolvent or solvent mixture of low volatility and/or a polar organicchemical solvent or solvent mixture and/or water, and if appropriate anemulsifier and/or wetting agent.

[0719] Organic chemical solvents which are preferably used are oily oroil-like solvents having an evaporation number above 35 and a flashpointabove 30° C., preferably above 45° C. Substances which are used as suchoily or oil-like water-insoluble solvents of low volatility areappropriate mineral oils or aromatic fractions thereof, or solventmixtures containing mineral oils, preferably white spirit, petroleumand/or alkylbenzene.

[0720] Mineral oils having a boiling range from 170 to 220° C., whitespirit having a boiling range from 170 to 220° C., spindle oil having aboiling range from 250 to 350° C., petroleum and aromatics having aboiling range from 160 to 280° C., terpentine oil and the like, areadvantageously employed.

[0721] In a preferred embodiment, liquid aliphatic hydrocarbons having aboiling range from 180 to 210° C. or high-boiling mixtures of aromaticand aliphatic hydrocarbons having a boiling range from 180 to 220° C.and/or spindle oil and/or monochloronaphthalene, preferably(α-monochloronaphthalene, are used.

[0722] The organic oily or oil-like solvents of low volatility whichhave an evaporation number above 35 and a flashpoint above 30° C.,preferably above 45° C., can be replaced in part by organic chemicalsolvents of high or medium volatility, providing that the solventmixture likewise has an evaporation number above 35 and a flashpointabove 30° C., preferably above 45° C., and that theinsecticide/fungicide mixture is soluble or emulsifiable in this solventmixture.

[0723] According to a preferred embodiment, some of the organic chemicalsolvent or solvent mixture is replaced by an aliphatic polar organicchemical solvent or solvent mixture. Aliphatic organic chemical solventscontaining hydroxyl and/or ester and/or ether groups, such as, forexample, glycol ethers, esters or the like, are preferably used.

[0724] Organic chemical binders which are used in the context of thepresent invention are the synthetic resins and/or binding drying oilswhich are known per se, are water-dilutable and/or are soluble ordispersible or emulsifiable in the organic chemical solvents employed,in particular binders consisting of or comprising an acrylate resin, avinyl resin, for example polyvinyl acetate, polyester resin,polycondensation or polyaddition resin, polyurethane resin, alkyd resinor modified alkyd resin, phenolic resin, hydrocarbon resin, such asindene-cumarone resin, silicone resin, drying vegetable oils and/ordrying oils and/or physically drying binders based on a natural and/orsynthetic resin.

[0725] The synthetic resin used as the binder can be employed in theform of an emulsion, dispersion or solution. Bitumen or bituminoussubstances can also be used as binders in an amount of up to 10% byweight. Dyestuffs, pigments, water-repelling agents, odour correctantsand inhibitors or anticorrosive agents and the like which are known perse can additionally be employed.

[0726] It is preferred according to the invention for the composition orconcentrate to comprise, as the organic chemical binder, at least onealkyd resin or modified alkyd resin and/or one drying vegetable oil.Alkyd resins having an oil content of more than 45% by weight,preferably 50 to 68% by weight, are preferably used according to theinvention.

[0727] All or some of the binder mentioned can be replaced by a fixingagent (mixture) or a plasticizer (mixture). These additives are intendedto prevent evaporation of the active compounds and crystallization orprecipitation. They preferably replace 0.01 to 30% of the binder (basedon 100% of the binder employed).

[0728] The plasticizers originate from the chemical classes of phthalicacid esters, such as dibutyl, dioctyl or benzyl butyl phthalate,phosphoric acid esters, such as tributyl phosphate, adipic acid esters,such as di-(2-ethylhexyl) adipate, stearates, such as butyl stearate oramyl stearate, oleates, such as butyl oleate, glycerol ethers or highermolecular weight glycol ethers, glycerol esters and p-toluenesulphonicacid esters.

[0729] Fixing agents are based chemically on polyvinyl alkyl ethers,such as, for example, polyvinyl methyl ether or ketones, such asbenzophenone or ethylenebenzophenone.

[0730] Possible solvents or diluents are, in particular, also water, ifappropriate as a mixture with one or more of the abovementioned organicchemical solvents or diluents, emulsifiers and dispersing agents.

[0731] Particularly effective preservation of wood is achieved byimpregnation processes on a large industrial scale, for example vacuum,double vacuum or pressure processes.

[0732] The ready-to-use compositions can also comprise otherinsecticides, if appropriate, and also one or more fungicides, ifappropriate.

[0733] Possible additional mixing partners are, preferably, theinsecticides and fungicides mentioned in WO 94/29 268. The compoundsmentioned in this document are an explicit constituent of the presentapplication.

[0734] Especially preferred mixing partners which may be mentioned areinsecticides, such as chlorpyriphos, phoxim, silafluofin, alphamethrin,cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25,flufenoxuron, hexaflumuron, transfluthrin, thiacloprid, methoxyfenozideand triflumuron, and also fungicides, such as epoxyconazole,hexaconazole, azaconazole, propiconazole, tebuconazole, cyproconazole,metconazole, imazalil, dichlorfluanid, tolylfluanid,3-iodo-2-propinyl-butyl carbamate, N-octyl-isothiazolin-3-one and4,5-dichloro-N-octylisothiazolin-3-one.

[0735] The compounds according to the invention can at the same time beemployed for protecting objects which come into contact with saltwateror brackish water, such as hulls, screens, nets, buildings, moorings andsignalling systems, against fouling.

[0736] Fouling by sessile Oligochaeta, such as Serpulidae, and by shellsand species from the Ledamorpha group (goose barnacles), such as variousLepas and Scalpellum species, or by species from the Balanomorpha group(acorn barnacles), such as Balanus or Pollicipes species, increases thefrictional drag of ships and, as a consequence, leads to a markedincrease in operation costs owing to higher energy consumption andadditionally frequent residence in the dry dock.

[0737] Apart from fouling by algae, for example Ectocarpus sp. andCeramium sp., fouling by sessile Entomostraka groups, which come underthe generic term Cirripedia (cirriped crustaceans), is of particularimportance.

[0738] Surprisingly, it has now been found that the compounds accordingto the invention, alone or in combination with other active compounds,have an outstanding antifouling action.

[0739] Using the compounds according to the invention, alone or incombination with other active compounds, allows the use of heavy metalssuch as, for example, in bis(trialkyltin) sulphides, tri-n-butyltinlaurate, tri-n-butyltin chloride, copper(I) oxide, triethyltin chloride,tri-n-butyl(2-phenyl-4-chlorophenoxy)tin, tributyltin oxide, molybdenumdisulphide, antimony oxide, polymeric butyl titanate,phenyl-(bispyridine)-bismuth chloride, tri-n-butyltin fluoride,manganese ethylenebisthiocarbamate, zinc dimethyldithiocarbamate, zincethylenebisthiocarbamate, zinc salts and copper salts of 2-pyridinethiol1-oxide, bisdimethyldithiocarbamoylzinc ethylene-bisthiocarbamate, zincoxide, copper(I) ethylene-bisdithiocarbamate, copper thiocyanate, coppernaphthenate and tributyltin halides to be dispensed with, or theconcentration of these compounds substantially reduced.

[0740] If appropriate, the ready-to-use antifouling paints canadditionally comprise other active compounds, preferably algicides,fungicides, herbicides, molluscicides, or other antifouling activecompounds.

[0741] Preferably suitable components in combinations with theantifouling compositions according to the invention are:

[0742] algicides such as

[0743] 2-tert-butylamino-4-cyclopropylamino-6-methylthio-1,3,5-triazine,dichlorophen, diuron, endothal, fentin acetate, isoproturon,methabenzthiazuron, oxyfluorfen, quinoclamine and terbutryn;

[0744] fungicides such as

[0745] benzo[b]thiophenecarboxylic acid cyclohexylamide S,S-dioxide,dichlofluanid, fluorfolpet, 3-iodo-2-propinyl butylcarbamate,tolylfluanid and azoles such as azaconazole, cyproconazole,epoxyconazole, hexaconazole, metconazole, propiconazole andtebuconazole;

[0746] molluscicides such as

[0747] fentin acetate, metaldehyde, methiocarb, niclosamid, thiodicarband trimethacarb; or conventional antifouling active compounds such as4,5-dichloro-2-octyl -4-isothiazolin-3-one, diiodomethylparatrylsulfone, 2-(N,N-dimethylthiocarbamoylthio)-5-nitrothiazyl, potassium,copper, sodium and zinc salts of 2-pyridinethiol 1-oxide,pyridine-triphenylborane, tetrabutyldistannoxane,2,3,5,6-tetrachloro-4-(methylsulfonyl )-pyridine,2,4,5,6-tetrachloroisophthalonitrile, tetramethylthiuram disulfide and2,4,6-trichlorophenylmaleiimide.

[0748] The antifouling compositions used comprise the active compoundaccording to the invention of the compositions according to theinvention in a concentration of 0.001 to 50% by weight, in particular0.01 to 20% by weight.

[0749] Moreover, the antifouling compositions according to the inventioncomprise the customary components such as, for example, those describedin Ungerer, Chem. Ind. 1985, 37, 730-732 and Williams, AntifoulingMarine Coatings, Noyes, Park Ridge, 1973.

[0750] Besides the algicidal, fungicidal, molluscicidal active compoundsand insecticidal active compounds according to the invention,antifouling paints comprise, in particular, binders.

[0751] Examples of recognized binders are polyvinyl chloride in asolvent system, chlorinated rubber in a solvent system, acrylic resinsin a solvent system, in particular in an aqueous system, vinylchloride/vinyl acetate copolymer systems in the form of aqueousdispersions or in the form of organic solvent systems,butadiene/styrene/acrylonitrile rubbers, drying oils such as linseedoil, resin esters or modified hardened resins in combination with tar orbitumens, asphalt and epoxy compounds, small amounts of chlorine rubber,chlorinated polypropylene and vinyl resins.

[0752] If appropriate, paints also comprise inorganic pigments, organicpigments or colorants which are preferably insoluble in salt water.Paints may furthermore comprise materials such as colophonium to allowcontrolled release of the active compounds. Furthermore, the paints maycomprise plasticizers, modifiers which affect the rheological propertiesand other conventional constituents. The compounds according to theinvention or the abovementioned mixtures may also be incorporated intoself-polishing antifouling systems.

[0753] The active compounds are also suitable for controlling animalpests, in particular insects, arachnids and mites, which are found inenclosed spaces such as, for example, dwellings, factory halls, offices,vehicle cabins and the like. They can be employed alone or incombination with other active compounds and auxiliaries in domesticinsecticide products for controlling these pests. They are activeagainst sensitive and resistant species and against all developmentalstages. These pests include:

[0754] From the order of the Scorpionidea, for example, Buthusoccitanus.

[0755] From the order of the Acarina, for example, Argas persicus, Argasreflexus, Bryobia spp., Dermanyssus gallinae, Glyciphagus domesticus,Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi,Neutrombicula autumnalis, Dermatophagoides pteronissimus,Dermatophagoides forinae.

[0756] From the order of the Araneae, for example, Aviculariidae,Araneidae.

[0757] From the order of the Opiliones, for example, Pseudoscorpioneschelifer, Pseudoscorpiones cheiridium, Opiliones phalangium.

[0758] From the order of the Isopoda, for example, Oniscus asellus,Porcellio scaber.

[0759] From the order of the Diplopoda, for example, Blaniulusguttulatus, Polydesmus spp.

[0760] From the order of the Chilopoda, for example, Geophilus spp.

[0761] From the order of the Zygentoma, for example, Ctenolepisma spp.,Lepisma saccharina, Lepismodes inquilinus.

[0762] From the order of the Blattaria, for example, Blatta orientalies,Blattella germanica, Blattella asahinai, Leucophaea maderae, Panchloraspp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana,Periplaneta brunnea, Periplaneta fuliginosa, Supella longipalpa.

[0763] From the order of the Saltatoria, for example, Acheta domesticus.

[0764] From the order of the Dermaptera, for example, Forficulaauricularia.

[0765] From the order of the Isoptera, for example, Kalotermes spp.,Reticulitermes spp.

[0766] From the order of the Psocoptera, for example, Lepinatus spp.,Liposcelis spp.

[0767] From the order of the Coleptera, for example, Anthrenus spp.,Attagenus spp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinusspp., Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae,Sitophilus zeamais, Stegobium paniceum.

[0768] From the order of the Diptera, for example, Aedes aegypti, Aedesalbopictus, Aedes taeniorhynchus, Anopheles spp., Calliphoraerythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culexpipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Muscadomestica, Phlebotomus spp., Sarcophaga carnaria, Simulium spp.,Stomoxys calcitrans, Tipula paludosa.

[0769] From the order of the Lepidoptera, for example, Achroia grisella,Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tineapellionella, Tineola bisselliella.

[0770] From the order of the Siphonaptera, for example, Ctenocephalidescanis, Ctenocephalides felis, Pulex irritans, Tunga penetrans,Xenopsylla cheopis.

[0771] From the order of the Hymenoptera, for example, Camponotusherculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus,Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.

[0772] From the order of the Anoplura, for example, Pediculus humanuscapitis, Pediculus humanus corporis, Phthirus pubis.

[0773] From the order of the Heteroptera, for example, Cimex hemipterus,Cimex lectularius, Rhodinus prolixus, Triatoma infestans.

[0774] In the field of household insecticides, they are used alone or incombination with other suitable active compounds, such as phosphoricacid esters, carbamates, pyrethroids, growth regulators or activecompounds from other known classes of insecticides.

[0775] They are used as aerosols, pressure-free spray products, forexample pump and atomizer sprays, automatic fogging systems, foggers,foams, gels, evaporator products with evaporator tablets made ofcellulose or polymer, liquid evaporators, gel and membrane evaporators,propeller-driven evaporators, energy-free, or passive, evaporationsystems, moth papers, moth bags and moth gels, as granules or dusts, inbaits for spreading or in bait stations.

[0776] The active compounds according to the invention can be used asdefoliants, desiccants, haulm killers and, especially, as weed killers.Weeds in the broadest sense are understood to mean all plants which growin locations where they are undesired. Whether the substances accordingto the invention act as total or selective herbicides dependsessentially on the amount used.

[0777] The active compounds according to the invention can be used, forexample, in connection with the following plants:

[0778] Dicotyledonous weeds of the genera: Abutilon, Amaranthus,Ambrosia, Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella,Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura,Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium,Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria,Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago,Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex,Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea,Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola,Xanthium.

[0779] Dicotyledonous crops of the genera: Arachis, Beta, Brassica,Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea,Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum,Vicia.

[0780] Monocotyledonous weeds of the genera: Aegilops, Agropyron,Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus,Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa,Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis,Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria,Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria,Scirpus, Setaria, Sorghum.

[0781] Monocotyledonous crops of the genera: Allium, Ananas, Asparagus,Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale,Triticum, Zea.

[0782] However, the use of the active compounds according to theinvention is in no way restricted to these genera, but also extends inthe same manner to other plants.

[0783] The active compounds according to the invention are suitable,depending on the concentration, for the total control of weeds, forexample on industrial terrain and rail tracks, and on paths and areaswith and without tree plantings. Similarly, the active compoundsaccording to the invention can be employed for controlling weeds inperennial crops, for example forests, decorative tree plantings,orchards, vineyards, citrus groves, nut orchards, banana plantations,coffee plantations, tea plantations, rubber plantations, oil palmplantations, cocoa plantations, soft fruit plantings and hop fields, onlawns, turf and pastureland, and for the selective control of weeds inannual crops.

[0784] The compounds according to the invention have strong herbicidalactivity and a broad active spectrum when used on the soil and onabove-ground parts of plants. To a certain extent they are also suitablefor the selective control of monocotyledonous and dicotyledonous weedsin monocotyledonous and dicotyledonous crops, both by the pre-emergenceand by the post-emergence method.

[0785] At certain concentrations or application rates, the activecompounds according to the invention can also be employed forcontrolling animal pests and fungal or bacterial plant diseases. Ifappropriate, they can also be used as intermediates or precursors forthe synthesis of other active compounds.

[0786] The active compounds can be converted into the customaryformulations such as solutions, emulsions, wettable powders,suspensions, powders, dusts, pastes, soluble powders, granules,suspension-emulsion concentrates, natural and synthetic materialsimpregnated with active compound, and microencapsulations in polymericmaterials.

[0787] These formulations are produced in a known manner, for example bymixing the active compounds with extenders, that is, liquid solventsand/or solid carriers, optionally with the use of surfactants, that is,emulsifiers and/or dispersants, and/or foam formers.

[0788] If the extender used is water, it is also possible, for example,to use organic solvents as cosolvents. The following are essentiallysuitable as liquid solvents: aromatics such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics and chlorinated aliphatichydrocarbons such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons such as cyclohexane or paraffins, forexample mineral oil fractions, mineral and vegetable oils, alcohols suchas butanol or glycol and their ethers and esters, ketones such asacetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,strongly polar solvents such as dimethylformamide and dimethylsulphoxide, or else water.

[0789] Suitable solid carriers are: for example ammonium salts andground natural minerals such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticmaterials such as highly-disperse silica, alumina and silicates;suitable solid carriers for granules are: for example crushed andfractionated natural rocks such as calcite, marble, pumice, sepioliteand dolomite, or else synthetic granules of inorganic and organic meals,and granules of organic material such as sawdust, coconut shells, maizecobs and tobacco stalks; suitable emulsifiers and/or foam formers are:for example nonionic and anionic emulsifiers such as polyoxyethylenefatty acid esters, polyoxyethylene fatty alcohol ethers, for examplealkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates,arylsulphonates, or else protein hydrolysates; suitable dispersants are:for example lignin-sulphite waste liquors and methylcellulose.

[0790] Tackifiers such as carboxymethylcellulose and natural andsynthetic polymers in the form of powders, granules or latices, such asgum arabic, polyvinyl alcohol and polyvinyl acetate, or else naturalphospholipids such as cephalins and lecithins and syntheticphospholipids can be used in the formulations. Other additives can bemineral and vegetable oils.

[0791] It is possible to use colorants such as inorganic pigments, forexample iron oxide, titanium oxide and Prussian Blue, and organiccolorants such as alizarin colorants, azo colorants and metalphthalocyanine colorants, and trace nutrients such as salts of iron,manganese, boron, copper, cobalt, molybdenum and zinc.

[0792] The formulations generally comprise between 0.1 and 95% by weightof active compound, preferably between 0.5 and 90%.

[0793] For controlling weeds, the active compounds according to theinvention, as such or in their formulations, can also be used asmixtures with known herbicides and/or substances which improve thecompatibility with crop plants (“safeners”), finished formulations ortank mixes being possible. Also possible are mixtures with weed-killerscomprising one or more known herbicides and a safener.

[0794] Possible components for the mixtures are known herbicides, forexample

[0795] acetochlor, acifluorfen (-sodium), aclonifen, alachlor, alloxydim(-sodium), ametryne, amicarbazone, amidochlor, amidosulfuron, anilofos,asulam, atrazine, azafenidin, azimsulfuron, BAS-662H, beflubutamid,benazolin (-ethyl), benfuresate, bensulfuron (-methyl), bentazon,benzfendizone, benzobicyclon, benzofenap, benzoylprop(-ethyl),bialaphos, bifenox, bispyribac (-sodium), bromobutide, bromofenoxim,bromoxynil, butachlor, butafenacil (-allyl), butroxydim, butylate,cafenstrole, caloxydim, carbetamide, carfentrazone (-ethyl),chlomethoxyfen, chloramben, chloridazon, chlorimuron (-ethyl),chlornitrofen, chlorsulfuron, chlortoluron, cinidon (-ethyl),cinmethylin, cinosulfuron, clefoxydim, clethodim, clodinafop(-propargyl), clomazone, clomeprop, clopyralid, clopyrasulfuron(-methyl), cloransulam (-methyl), cumyluron, cyanazine, cybutryne,cycloate, cyclosulfamuron, cycloxydim, cyhalofop (-butyl), 2,4-D,2,4-DB, desmedipham, diallate, dicamba, dichlorprop (-P), diclofop(-methyl), diclosulam, diethatyl (-ethyl), difenzoquat, diflufenican,diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn,dimethenamid, dimexyflam, dinitramine, diphenamid, diquat, dithiopyr,diuron, dymron, epropodan, EPTC, esprocarb, ethalfluralin,ethametsulfuron (-methyl), ethofumesate, ethoxyfen, ethoxysulfuron,etobenzanid, fenoxaprop (-P-ethyl), fentrazamide, flamprop (-isopropyl,-isopropyl-L, -methyl), flazasulfuron, florasulam, fluazifop (-P-butyl),fluazolate, flucarbazone (-sodium), flufenacet, flumetsulam, flumiclorac(-pentyl), flumioxazin, flumipropyn, flumetsulam, fluometuron,fluorochloridone, fluoroglycofen (-ethyl), flupoxam, flupropacil,flurpyrsulfuron (-methyl, -sodium), flurenol (-butyl), fluridone,fluroxypyr (-butoxypropyl, -meptyl), flurprimidol, flurtamone,fluthiacet (-methyl), fluthiamide, fomesafen, foramsulfuron, glufosinate(-ammonium), glyphosate (-isopropylammonium), halosafen, haloxyfop(-ethoxyethyl, -P-methyl), hexazinone, imazamethabenz (-methyl),imazamethapyr, imazamox, imazapic, imazapyr, imazaquin, imazethapyr,imazosulfuron, iodosulfuron (-methyl, -sodium), ioxynil, isopropalin,isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole,isoxapyrifop, lactofen, lenacil, linuron, MCPA, mecoprop, mefenacet,mesotrione, metamitron, metazachlor, methabenzthiazuron, metobenzuron,metobromuron, (alpha-) metolachlor, metosulam, metoxuron, metribuzin,metsulfuron (-methyl), molinate, monolinuron, naproanilide, napropamide,neburon, nicosulfuron, norflurazon, orbencarb, oryzalin, oxadiargyl,oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat,pelargonic acid, pendimethalin, pendralin, pentoxazone, phenmedipham,picolinafen, piperophos, pretilachlor, primisulfuron (-methyl),profluazol, prometryn, propachlor, propanil, propaquizafop,propisochlor, propoxycarbazone (-sodium), propyzamide, prosulfocarb,prosulfuron, pyraflufen (-ethyl), pyrazogyl, pyrazolate, pyrazosulfuron(-ethyl), pyrazoxyfen, pyribenzoxim, pyributicarb, pyridate, pyridatol,pyriftalid, pyriminobac (-methyl), pyrithiobac (-sodium), quinchlorac,quinmerac, quinoclamine, quizalofop (-P-ethyl, -P-tefuryl), rimsulfuron,sethoxydim, simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron(-methyl), sulfosate, sulfosulfuron, tebutam, tebuthiuron, tepraloxydim,terbuthylazine, terbutryn, thenylchlor, thiafluamide, thiazopyr,thidiazimin, thifensulfuron (-methyl), thiobencarb, tiocarbazil,tralkoxydim, triallate, triasulfuron, tribenuron (-methyl), triclopyr,tridiphane, trifluralin, trifloxysulfuron, triflusulfuron (-methyl),tritosulfuron.

[0796] A mixture with other known active compounds, such as fungicides,insecticides, acaricides, nematicides, bird repellents, plant nutrientsand agents which improve soil structure, is also possible.

[0797] The active compounds can be used as such, in the form of theirformulations or in the use forms prepared therefrom by further dilution,such as ready-to-use solutions, suspensions, emulsions, powders, pastesand granules. They are used in a customary manner, for example bywatering, spraying, atomizing or broadcasting.

[0798] The active compounds according to the invention can be appliedboth before and after emergence of the plants. They can also beincorporated into the soil before sowing.

[0799] The amount of active compound used can vary within a relativelywide range. It depends essentially on the nature of the desired effect.In general, the amounts used are between 1 g and 10 kg of activecompound per hectare of soil surface, preferably between 5 g and 5 kgper ha.

[0800] The preparation and the use of the active compounds according tothe invention is illustrated by the examples below.

PREPARATION EXAMPLES Example I-1-A-a-1

[0801]

[0802] At 0° C., 3.70 g (0.031 mol) of potassium tert-butoxide areinitially charged in 26 ml of anhydrous DMF, and 6 g of the compoundaccording to Example II-1in 12 ml of anhydrous DMF are added. Themixture is stirred at 20° C. for 1 h.

[0803] The reaction solution is added to 200 ml of ice-water andacidified at 0-10° C. The precipitate is then filtered off with suctionand recrystallized.

[0804] Yield: 4.66 g ({circumflex over (=)}83% of theory), m.p..>260° C.

[0805] DMF (dimethylformamide)

[0806] The following compounds of the formula (I-1-A-a) are obtainedsimilarly to Example (I-1-A-a-1) and in accordance with the generalstatements on the preparation (I-1-A-a)

Ex. No. X Y D A B m.p. ° C. isomer I-1-A-a-2 —CH₃ 4-Cl—C₆H₄ H CH₃ CH₃230 — I-1-A-a-3 —CH₃ 4-Cl—C₆H₄ H —(CH₂)₂—CHOCH₃—(CH₂)₂— 246 β I-1-A-a-4—CH₃ 4-Cl—C₆H₅ H —(CH₂)₂—CHOC₂H₅—(CH₂)₂— >250 β I-1-A-a-5 —CH₃ 4-Cl—C₆H₄H —(CH₂)₂O—(CH₂)₂— >265 — I-1-A-a-6 —CH₃ 4-Cl—C₆H₄ H —CH₂—O—(CH₂)₃— >250— I-1-A-a-7 —C₂H₅ 4-Cl—C₆H₄ H —(CH₂)₂—CHOCH₃—(CH₂)₂— 250 β I-1-A-a-8—CH₃ 4-CH₃—C₆H₄ H —(CH₂)₂—CHOCH₃—(CH₂)₂— 244 β I-1-A-a-9 —CH₃ CH₃ H—(CH₂)₂—CHOCH₃—(CH₂)₂— 406 β I-1-A-a-10 —C₂H₅ 4-Cl—C₆H₄ H CH₃ CH₃ 176 —I-1-A-a-11 —CH₃ C₆H₅ H —(CH₂)₂—CHOCH₃—(CH₂)₂— 235 β I-1-A-a-12 —CH₃2-Cl, 6-OCH₃—C₆H₃ H —(CH₂)₂—CHOCH₃—(CH₂)₂— 249 β I-1-A-a-13 —CH₃4-CH₃—C₆H₄ H CH₃ CH₃ 228 — I-1-A-a-14 —CH₃ C₆H₅ H CH₃ CH₃ 177 —I-1-A-a-15 —C₃H₇ 4-Cl—C₆H₄ H —(CH₂)₂—CHOCH₃—(CH₂)₂— 204 β I-1-A-a-16—CH₃ 2-Cl—C₆H₄ H —(CH₂)₂—CHOCH₃—(CH₂)₂— 235 β I-1-A-a-17 —CH₃2,4-Cl₂—C₆H₃ H —(CH₂)₂—CHOCH₃—(CH₂)₂— 235 β I-1-A-a-18 —CH₃ 4-CF₃—C₆H₄ H—(CH₂)₂—CHOCH₃—(CH₂)₂— 258 β I-1-A-a-19 —CH₃ 3-CF₃—C₆H₄ H CH₃ CH₃ 172 —I-1-A-a-20 —CH₃ 2,4-Cl₂—C₆H₃ H CH₃ CH₃ 211 — I-1-A-a-21 —CH₃ 4-CF₃—C₆H₄H CH₃ CH₃ 220 — I-1-A-a-22 —CH₃ 2-Cl—C₆H₄ H CH₃ CH₃ 218 — I-1-A-a-23—C₃H₇ 4-Cl—C₆H₄ H CH₃ CH₃ — I-1-A-a-24 Br 4-Cl—C₆H₄ H—(CH₂)₂—CHOCH₃—(CH₂)₂— β I-1-A-a-25 CH₃

H —(CH₂)₂—CHOCH₃—(CH₂)₂— β I-1-A-a-26 Cl 4-Cl—C₆H₄ H—(CH₂)₂—CHOCH₃—(CH₂)₂— β I-1-A-a-27 Br 4-Cl—C₆H₄ H CH₃ CH₃ 143 —I-1-A-a-28 Cl 4-Cl—C₆H₄ H CH₃ CH₃ 208 — I-1-A-a-29 CH₃

H CH₃ CH₃ 226 — I-1-A-a-30 CH₃ 4-Cl—C₆H₄— H

β I-1-A-a-31 C₃H₇ 4-Cl—C₆H₄ H CH₃ CH₃ 162 — I-1-A-a-32 CH₃ 2-Cl—C₆H₄ H—(CH₂)₂—CHOCH₃—(CH₂)₂— 261 α I-1-A-a-33 CH₃ 3-Cl—C₆H₄ H—(CH₂)₂—CHOCH₃—(CH₂)₂— 245 β I-1-A-a-34 CH₃ 3-Cl—C₆H₄ H CH₃ CH₃ 212 —I-1-A-a-35 CH₃ 4-Cl—C₆H₄—CH₂— H CH₃ CH₃ 139 — I-1-A-a-36 CH₃ 4-CF₃—C₆H₄H —(CH₂)₂—CHOCH₃—(CH₂)₂— 220 α I-1-A-a-37 CH₃ 4-Cl—C₆H₄—CH₂— H—(CH₂)₂—CHOCH₃—(CH₂)₂ — 205 β I-1-A-a-38 i-C₃H₇ 4-Cl—C₆H₄ H—(CH₂)₂—CHOCH₃—(CH₂)₂— 274 β I-1-A-a-39 CH₃

H CH₃ CH₃ 181 — I-1-A-a-40 CH₃

H CH₃ CH₃ 205 — I-1-A-a-41 CH₃

H CH₃ CH₃ 254 — I-1-A-a-42 CH₃

H —(CH₂)₂—CHOCH₃—(CH₂)₂— 252 β I-1-A-a-43 CH₃ 4-(CH₃)₃C—C₆H₄ H—(CH₂)₂—CHOCH₃—(CH₂)₂— 252 β I-1-A-a-44 CH₃ 4-(Cl—C₆H₄ H—(CH₂)₂—C(CH₃)₂—(CH₂)₂— 291 — I-1-A-a-45 CH₃ 4-Cl—C₆H₄ —(CH₂)₂—S—CH₂— H197 — I-1-A-a-46 CH₃

H —(CH₂)₂—CHOCH₃—(CH₂)₂— 252 α I-1-A-a-47 CH₃

H CH₃ CH₃ 121 — I-1-A-a-48 CH₃ 4-Cl—C₆H₄ —(CH₂)₄— H

Example I-1-A-b-1

[0807]

[0808] 0.81 g of the compound according to Example I-1-a-2 is initiallycharged in 10 ml of anhydrous ethyl acetate and heated at reflux with0.3 ml (2.2 mmol) of triethylamine. 0.25 ml (0.0022 mol) of isobutyrylchloride in 5 ml of anhydrous ethyl acetate is then added, and themixture is heated at reflux.

[0809] After the reaction has ended (TLC), the solvent is distilled offand the residue is taken up in dichloromethane, washed twice with 10 mlof 0.5 N NaOH, dried and concentrated using a rotary evaporator. Theresidue is purified by silica gel column chromatography(dichloromethane/ethyl acetate, 3:1).

[0810] Yield: 0.2 g ({circumflex over (=)}21% of theory) m.p. 208° C.

[0811] The following compounds of the formula (I-1-A-b) are obtainedsimilarly to Example (I-1-A-b-1) and in accordance with the generalstatements on the preparation (I-1-A-b)

Ex. No X Y D A B R¹ m.p. ° C. isomer I-1-A-b-2 CH₃ 4-Cl—C₆H₄ H—(CH₂)₂—CHOCH₃—(CH₂)₂—

273 — I-1-A-b-3 CH₃ 4-Cl—C₆H₄ H —(CH₂)₂—CHOCH₃—(CH₂)₂—

249 β

Example I-1-A-c-1

[0812]

[0813] 0.69 g of the compound according to Example I-1-a-2 is initiallycharged in 10 ml of anhydrous dichloromethane and, at 10° C., admixedwith 0.24 ml (1.7 mmol) of triethylamine.

[0814] 0.17 ml (1.7 mmol) of ethyl chloroformate in 1 ml of anhydrousdichloromethane is then added, and the mixture is stirred at roomtemperature.

[0815] After the reaction has ended (TLC), the solvent is distilled offand the residue is taken up in dichloromethane, washed twice with 10 mlof 0.5 N NaOH, dried and concentrated using a rotary evaporator. Theresidue is purified by silica gel column chromatography(dichloromethane/ethyl acetate, 3:1).

[0816] Yield: 0.58 g ({circumflex over (=)}71% of theory), m.p. 211° C.

[0817] The following compounds of the formula (I-1-A-c) are obtainedsimilarly to Example (I-1-A-c-1) and in accordance with the generalstatements on the preparation (I-1-A-c)

Ex. No. X Y D A B L M R² m.p. ° C. isomer I-1-A-c-2 CH₃ 4-Cl—C₆H₄ H—(CH₂)₂—CHOCH₃—(CH₂)₂— O O

— β I-1-A-c-3 CH₃ 4-Cl—C₆H₄ H —(CH₂)₂—CHOCH₃—(CH₂)₂— O O

292 β I-1-A-c-4 CH₃ CH₃ H —(CH₂)₂—CHOCH₃—(CH₂)₂— O O C₂H₅ — β

Example II-A-1

[0818]

[0819] 6.6 ml of triethylamine are added to 4.61 g of methyl4-methyl-1-amino-cyclohexane-1-carboxylate hydrochloride in 80 ml ofanhydrous tetrahydrofuran, and the mixture is stirred for 3 min. 5.3 gof 4-[2-(4-chlorophenyl)-5-methyl]-thiazolyl-acetic acid are added. Themixture is stirred at room temperature for another 15 min. 4.4 ml oftriethylamine are then added, followed immediately by dropwise additionof 1.12 ml of phosphorus oxychloride such that the solution boilsmoderately. The solution is heated at reflux for 30 min.

[0820] The reaction solution is poured into 200 ml of ice-water,extracted with dichloromethane and dried. The solvent is distilled offand the residue is recrystallized.

[0821] Yield: 6.19 g ({circumflex over (=)}73% of theory), m.p.: 150° C.

[0822] The following compounds of the formula (II-A) are obtainedsimilarly to Examples (II-A-1) and (II-A-48) and in accordance with thegeneral statements on the preparation (II-A)

Ex. No. X Y D A B R⁸ m.p. ° C. isomer II-A-2 CH₃ 4-Cl—C₆H₄ H—(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 121 β II-A-3 CH₃ 4-Cl—C₆H₄ H—(CH₂)₂—CHOC₂H₅—(CH₂)₂— CH₃ 120 β II-A-4 CH₃ 4-Cl—C₆H₄ H—(CH₂)₂—O—(CH₂)₂— CH₃ 201 — II-A-5 CH₃ 4-Cl—C₆H₄ H —CH₂—O—(CH₂)₃— CH₃132 — II-A-6 CH₃ 4-Cl—C₆H₄ H CH₃ CH₃ CH₃ 139 — II-A-7 C₂H₅ 4-Cl—C₆H₄ H—(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 124 β II-A-8 C₂H₅ 4-Cl—C₆H₄ H CH₃ CH₃ CH₃ 106— II-A-9 C₂H₅ 4-CH₃—C₆H₄ H CH₃ CH₃ CH₃ 164 — II-A-10 CH₃ C₆H₅ H CH₃ CH₃CH₃ 142 — II-A-11 CH₃ 4-CH₃—C₆H₄ H —(CH₂)₂—CHOCH₃13 (CH₂)₂— CH₃ 119 βII-A-12 CH₃ C₆H₅ H —(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 143 β II-A-13 CH₃ CH₃ H—(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ ÖI β II-A-14 CH₃ 2-Cl, 6-F—C₆H₃ H—(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ ÖI β II-A-15 C₃H₇ 4-Cl—C₆H₄ H —(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 114 β II-A-16 CH₃ 2-Cl—C₆H₄ H—(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 128 β II-A-17 C₃H₇ 4-Cl—C₆H₄ H CH₃ CH₃ CH₃129 — II-A-18 CH₃ 2-Cl—C₆H₄ H CH₃ CH₃ CH₃ 112 — II-A-19 CH₃ 2,4-Cl₂—C₆H₃H CH₃ CH₃ CH₃ 136 — II-A-20 CH₃ 4-CF₃—C₆H₄ H CH₃ CH₃ CH₃ 119 — II-A-21CH₃ 2,4-Cl₂C₆H₃ H —(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 124 β II-A-22 CH₃4-CF₃—C₆H₄ H —(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 110 β II-A-23 CH₃ 3-Cl—C₆H₄ H—(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 130 β II-A-24 CH₃ 3-Cl—C₆H₄ H CH₃ CH₃ CH₃ 135— II-A-25 CH₃ 3-CF₃—C₆H₄ H CH₃ CH₃ CH₃ 160 — II-A-26 Cl 4-Cl—C₆H₄ H—(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 129 β II-A-27 CH₃

H —(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 168 β II-A-28 Br 4-Cl—C₆H₄ H CH₃ CH₃ CH₃127 — II-A-29 CH₃ 3,4-Cl₂—C₆H₃ H CH₃ CH₃ CH₃ 163 — II-A-30 CH₃

H CH₃ CH₃ CH₃ 160 — II-A-31 Cl 4-Cl—C₆H₄ H CH₃ CH₃ CH₃ 144 — II-A-32i-C₃H₇ 4-Cl—C₆H₄ H —(CH₂)₂—(CHOCH₃—(CH₂)₂— CH₃ 123 β II-A-33 CH₃4-Cl—C₆H₄—CH₂ H —(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 108 β II-A-34 CH₃4-Cl—C₆H₄—CH₂ H CH₃ CH₃ CH₃ 109 — II-A-35 CH₃

H —(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 108 β II-A-36 CH₃

H CH₃ CH₃ CH₃ 132 — II-A-37 CH₃

H CH₃ CH₃ CH₃ ÖI — II-A-38 CH₃

H —(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 118 β II-A-39 CH₃ 4-Cl—C₆H₄ H—(CH₂)₂—C(CH₃)₂—(CH₂)₂— CH₃ 177 — II-A-40 CH₃

H —(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 157 β II-A-41 CH₃

H —(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 137 β II-A-42 CH₃ 4-(CH₃)₃C—C₆H₄ H—(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ β II-A-43 CH₃

H CH₃ CH₃ CH₃ 125 — II-A-44 CH₃

H CH₃ CH₃ CH₃ 146 — II-A-45 CH₃ 4-Cl—C₆H₄ —(CH₂)₄— H C₂H₅ ÖI — II-A-46CH₃ 4-Cl—C₆H₄ —(CH₂)₂—S—CH₂— H C₂H₅ ÖI — II-A-47 CH₃ 4-Cl—C₆H₄ i-C₃H₇ HH C₂H₅ ÖI — II-A-48 CH₃ 4-Cl—C₆H₄ H

CH₃ CH₃ II-A-49 CH₃ 4-Cl—C₆H₄ H i-C₃H₇ CH₃ CH₃ II-A-50 CH₃ 4-Cl—C₆H₄ H

CH₃ β II-A-51 CH₃ 4-Cl—C₆H₄ H

CH₃ α II-A-52 Br 4-Cl—C₆H₄ H —(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 127 β II-A-53CH₃ 3,4-Cl₂—C₆H₃ H —(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ β II-A-54 CH₃ 4-Br—C₆H₄ H—(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 136 β

Example No. II-A-48

[0823]

[0824] 7.4 g (0.075 mol) of concentrated sulphuric acid are initiallycharged, and 5.37 g of the compound according to Preparation ExampleXXI-A-1 in 30 ml of methylene chloride are then added dropwise at aninternal temperature of from 30 to 40° C. The mixture is then stirred atfrom 30 to 40° C. for 2 hours. 11 ml of absolute methanol are addeddropwise such that an internal temperature of 40° C. results. Stirringis continued at from 40 to 70° C. for 6 hours.

[0825] The reaction solution is poured onto 0.08 kg of ice. The mixtureis extracted with dichloromethane, the extract is washed with NaHCO₃solution and dried and the solvent is distilled off. The residue is thenpurified by silica gel column chromatography (dichloromethane/ethylacetate, 5:1).

[0826] This gives 0.42 g ({circumflex over (=)}7% of theory), m.p. 131°C.

Example XXI-A-1

[0827]

[0828] 3.7 g of 2-amino-2-cyclopropyl-propionitrile in 60 ml of absolutetetrahydrofuran and 4.92 ml of triethylamine are stirred for 5 min. 8.03g of 5-methyl-2-(4-chloro-phenyl)-thiazolylacetic acid are then added,and the mixture is stirred at room temperature for 15 min. 6.6 ml oftriethylamine are added, followed immediately by dropwise addition of1.68 ml of phosphorus oxychloride such that the solution boilsmoderately.

[0829] The solution is stirred at reflux for 30 min. The solvent is thendistilled off and the residue is purified by silica gel columnchromatography (n-hexane/ethyl acetate, 2:1).

[0830] Yield: 5.37 g (49% of theory), m.p. 114° C.

[0831] The following compounds of the formula (XXI-A)are obtainedsimilarly to Example (XXI-A-1) and in accordance with the generalstatements on the preparation (XXI-A)

Ex. No. X Y D A B m.p. ° C. XXI-1-A-2 CH₃ 4-Cl—C₆H₄ H—(CH₂)₂—C(CH₃)₂—(CH₂)₂— 147 XXI-1-A-3 CH₃ 4-Cl—C₆H₄ H i-C₃H₇ CH₃ 134XXI-1-A-4 CH₃ 4-Cl—C₆H₄ H

151

Example I-2-A-a-1

[0832]

[0833] With ice-cooling 6.6 of 1 m potassium tert-butoxide solution areadded to 2.48 g (5.49) mmol) of the compound according to Example III-1in 10 ml of anhydrous DMF, and the mixture is stirred at roomtemperature overnight. The solvent is distilled off and the residue isdissolved in water, acidified slowly with conc. HCl, filtered off withsuction and dried. Yield: 2 g({circumflex over (=)}89% of theory), m.p.117-120° C.

[0834] The following compounds of the formula (I-2-A-a) are obtainedsimilarly to Example (I-2-A-a-1) and in accordance with the generalstatements on the preparation (I-2-A-a)

Ex. No. X Y A B m.p. ° C. I-2-A-a-2 CH₃ 4-Cl—C₆H₄ CH₃ CH₃ 133-135I-2-A-a-3 CH₃ C₆H₅ —(CH₂)₂—CHOCH₃—(CH₂)₂— I-2-A-a-4 CH₃ C₆H₅ CH₃ CH₃

[0835] Ex. No. I-2-A-a-3δ=1.45-2.25 (m, 8H), 2.90/3.00 (2s, 3H),3.30/3.40 (2s, 3H), 3.25/3.50 (2m, 1H), 7.35-8.25 (m, 5H).

[0836] Ex. No. I-2-A-a-4δ=1.60 (s, 6H), 2.95 (s, 3H), 7.45 (m, 3H), 7.80(m, 2 H).

Example I-2-A-b-1

[0837]

[0838] At from 0 to 1020 C., 0.244 g (2.3 mmol) of isobutyryl chlorideis added to 0.7 g (2.1 mmol) of the compound according to PreparationExample III-A-2 in absolute dichloromethane and 0.232 g (2.3 mmol) oftriethylamine, and the mixture is stirred at room temperature for 8hours. The reaction solution is washed with 10% citric acid and 10% NaOHsolution. The organic phase is separated off, dried and concentrated.

[0839] The residue is purified by silica gel column chromatography(dichloromethane/ethyl acetate, 20/1).

[0840] Yield: 0.1 g {circumflex over (=)}11.8% of theory, m.p. 95-98° C.

Example I2-A-c-1

[0841]

[0842] At from 0 to 10° C, isopropyl chloroformate (0.249 g, 2 mmol, 1 Min toluene) is added to 0.75 g (1.85 mmol) of Example I-2-A-1 inabsolute dichloromethane and 0.206 g (2 mmol) of triethylamine. Themixture is stirred at room temperature for 8 hours and then washed with10% citric acid solution and with 10% strength NaOH solution. Theorganic phase is separated off and dried, and the solvent is removed bydistillation.

[0843] The residue is purified by silica gel column chromatography(dichloromethane/ethyl acetate, 20/1).

[0844] Yield: 0.37 g {circumflex over (=)}40% of theory, m.p. 140-145°C.

Example III-A-1

[0845]

[0846] 1.11 g (5.49 mmol) of ethyl4-methoxy-1-hydroxy-cyclohexane-1-carboxylate and 1.57 g (5.49 mmol) ofthe compound according to Example XVI-1 are stirred at 140° C. for 6 h,the mixture is cooled and the HCl gas is flushed out using argon.

[0847] Yield: 2.4 g ({circumflex over (=)}41.62% of theory), logP(acidic) 4.54 (HPLC; acetonitrile).

[0848] The following compounds of the formula (III-A) are preparedanalogously to Example (III-A-1) and in accordance with the generalstatements on the preparation (III-A)

Ex. No. X Y A B R⁸ m.p. ° C. III-A-2 CH₃ 4-Cl—C₆H₄ CH₃ CH₃ C₂H₅ logP_((pH2)) 4.53 III-A-3 CH₃ C₆H₅ —(CH₂)₂—CHOCH₃—(CH₂)₂— C₂H₅ III-A-4 CH₃C₆H₅ CH₃ CH₃ C₂H₅

Example I-3-A-a-1

[0849]

[0850] 15 g (20 mmol) of the compound according to Example (IV-A-1) areinitially charged in 22 ml of trifluoroacetic acid (TFA) and 51 ml oftoluene, and the mixture is heated at reflux overnight. The solvent andthe TFA are distilled off and the residue is taken up in 200 ml of waterand 200 ml of methyl tert-butyl ether. The organic phase is extractedwith alkali, the aqueous phase is acidified and extracted withdichloromethane, the organic extract is dried and the solvent isdistilled off.

[0851] The residue is purified by silica gel column chromatography(dichloromethane/ethyl acetate, 10:1→5:1).

[0852] Yield: 1.6 g (23% of theory), m.p. 132-135° C.

Example I-3-A-c-1

[0853]

[0854] 500 mg (1.4 mmol) of the compound according to Example(I-3-A-a-1) are initially charged in 5 ml of absolute dichloromethaneand mixed with 0.29 ml (2.1 mmol, 1.5 eq) of triethylamine, and 0.2 g(1.8 mmol, 1.3 eq) of ethyl chloroformate are added with ice-cooling.

[0855] The mixture is stirred at room temperature for 2 hours, washedwith 10% strength citric acid, extracted with dichloromethane, washedwith 1 N NaOH and extracted with dichloromethane. The extract is driedand the solvent is distilled off.

[0856] Yield: 0.55 g (93% of theory) oil. ¹H-NMR (d₆-DMSO, 400 MHz):δ=0.93 (t, 3H, +E,uns, CH ³ —CH₂), 1.75 (s, 6H, 2 CH ³ —C), 2.37 (s, 3H,CH₃—C arom.), 3.98 (q, 2H, CH₃—CH ² ), 7.55 (d, 2H, 2 CH arom.), 7.87(d, 2H, 2 CH arom.) ppm.

Example IV-A-1

[0857]

[0858] 4.8 g (20.0 mmol) of 2-(4-methoxy-benzylthio)-2-methyl-propionicacid are initially charged in 40 ml of anhydrous toluene and 1 drop ofDMF, and 7.2 g (60 mmol, 4 ml) of thionyl chloride are added. Themixture is stirred at room temperature for 5 min and then at 100° C.until evolution of gas has ceased. The solvent is distilled off and theresidue is taken up in 10 ml of anhydrous tetrahydrofuran (solution A).

[0859] 17.1 ml of lithium diisopropylamide are initially charged at 0°C. in 40 ml of anhydrous tetrahydrofuran, and 10.1 g (32.7 mmol) ofmethyl 4-[5-methyl-2-(4-chloro-phenyl)]-thiazolylacetate in 10 ml ofanhydrous tetrahydrofuran are added dropwise at 0° C., and the mixtureis stirred for another 30 min. Solution A is then added dropwise at 0°C., and the mixture is stirred at room temperature for 1 h. The reactionmixture is then admixed with 100 ml of MTB ether and a few drops ofwater and washed 2× with in each case 100 ml of 10% strength NH₄Clsolution. The organic phase is dried and the solvent is distilled off.The crude product is reacted without further purification.

[0860] Yield: 15.2 g (100% of theory).

[0861]¹H-NMR (DMSO, 400 MHz): δ=1.43 (s, 3H, CH ³ —C aliph.), 1.50 (s,3H, CH ³ —C aliph.), 2.40 (s, 3H, CH ₃—C heteroatom.), 3.31 (s, 2H,CH₂), 3.61 (s, 3H, CH₃—OCO), 3.82 (s, 3H, CH₃—O) ppm.

Example XVI-1

[0862]

[0863] 3 g (11.21 mmol) of4-[2-(4-chlorophenyl)-5-methyl]-thiazolyl-acetic acid are initiallycharged in 50 ml of absolute dichloromethane. With ice-cooling, 2.13 g(16.81 mmol) of oxalyl chloride are slowly added dropwise, the mixtureis stirred at room temperature overnight and then heated at reflux for 2h, and the solvent is distilled off.

[0864] Yield: 3.19 g (96% of theory).

Example I-1-B-a-1

[0865]

[0866] At 20° C., 3.59 g of the compound according to PreparationExample II-B-1 in 7 ml of anhydrous DMF are added dropwise to 2.41 g(0.020 mol) of potassium tert-butoxide in 17 ml of anhydrousdimethylformamide (DMF), and the mixture is stirred at 40° C. for 1hour.

[0867] The reaction solution is stirred into 100 ml of ice-water and, atfrom 0 to 10° C., acidified with hydrochloric acid. The precipitate isfiltered off with suction and chromatographed on silica gel usingmethylene chloride/acetone 5:1.

[0868] Yield: 1.2 g (36% of theory), m.p.>240° C.

[0869] The Following compounds of the formula (I-1-B-a) are obtainedsimilarly to Example (I-1-B-a-1) and in accordance with the generalstatements on the preparation (I-1-B-a)

Ex. No. X Y D A B m.p. ° C. isomer I-1-B-a-2 CH₃ C₆H₆ H CH₃ CH₃ 187 —I-1-B-a-3 CH₃ 4-Cl—C₆H₄ H —(CH₂)₂—CHOCH₃—(CH₂)₂— 279 β

Example II-B-1

[0870]

[0871] 4.56 g (20 mmol) of methyl1-amino-4-methoxy-cyclohexanecarboxylate hydrochloride are initiallycharged in 60 ml of absolute THF, admixed with 6 ml of triethylamine andstirred for 5 min. 3.27 g of 4-(2-phenyl-5-methyl)-oxazolyl-acetic acidare added, and the mixture is stirred at room temperature for 15 min.3.3 ml of triethylamine are added and 0.84 ml of phosphorus oxychlorideis added dropwise such that the solution boils moderately.

[0872] The mixture is stirred at reflux for 30 min.

[0873] The solvent is distilled off and the precipitate is purified bysilica gel column chromatography (dichloromethane/ethyl acetate, 3:1).

[0874] Yield: 3.5 g (61% of theory), m.p. 125° C.

[0875] The following compounds of the formula (II-B) are obtainedsimilarly to Example (II-B-1) and in accordance with the generalstatements on the preparation (II-B)

Ex. No. X Y D A B R⁸ m.p. ° C. isomer II-B-2 CH₃ C₆H₅ H CH₃ CH₃ CH₃ 101— II-B-3 CH₃ 4-Cl—C₆H₄ H —(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 95 β

Example I-2-B-a-1

[0876]

[0877] In the absence of a solvent, 1.01 g (5 mmol) of ethyl4-methoxy-1-hydroxy-cyclohexane-1-carboxylate and 1.095 g (5 mmol) of2-phenyl-4-methyl-isoxazol-3-acetyl chloride were heated at 140° C.overnight and then briefly degassed under reduced pressure. Theresulting crude product was dissolved in 10 ml of DMF. 6 ml of a 1Msolution of KOtBu in DMF were metered in over a period of 10 min, themixture was stirred at room temperature overnight and then evaporated todryness using a rotary evaporator, the residue was dissolved in waterand extracted 1× with ethyl acetate to remove impurities, 10 ml of 1Nhydrochloric acid were slowly metered in (until the mixture was acidic)and the precipitated product was filtered off with suction. Furtherpurification was carried out by preparative HPLC (acetonitrile/water onRP-18):

[0878] Yield: 0.33 g (19% of theory), m.p. 65° C.

[0879]¹H-NMR MHz (CDCl₃): δ=1.60-2.30 (m, 8H), 2.85 (s, 3H), 3.30/3.40(2s, 3H), 3.30/3.60 (2 m, 1H), 7.40-8.00 (m, 5H).

[0880] The following compounds of the formula (I-2-B-a) are obtainedsimilarly to Example (I-2-B-a-1) and in accordance with the generalstatements on the preparation (I-2-B-a)

Ex. No. X Y A B m.p. ° C. I-2-B-a-2 CH₃ C₆H₅ CH₃ CH₃ log P _((pH2)) 3.43

Use Examples Example A

[0881] Meloidogyne Test Solvent: 30 parts by weight of dimethylformamideEmulsifier: 1 part by weight of alkylaryl polyglycol ether

[0882] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amounts of solventand emulsifier, and the concentrate is diluted with water to the desiredconcentration.

[0883] Containers are filled with sand, solution of active compound,Meloidogyne incognita egg/larvae suspension and lettuce seeds. Thelettuce seeds germinate and the plants develop. On the roots, galls areformed.

[0884] After the desired period of time, the nematicidal action in % isdetermined using the formation of galls as a measure. 100% means that nogalls have been found; 0% means that the number of galls on the treatedplants corresponds to that on the untreated control.

[0885] In this test, for example, the following compounds of thePreparation Examples show good activity: I2-a-1 and I-2-a-2.

Example B

[0886] Myzus Test Solvent: 30 parts by weight of dimethylformamideEmulsifier: 1 part by weight of alkylaryl polyglycol ether

[0887] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amounts of solventand emulsifier, and the concentrate is diluted withemulsifier-containing water to the desired concentration.

[0888] Cabbage leaves (Brassica oleracea) which are heavily infested bythe peach aphid (Myzus persicae) are treated by being dipped into thepreparation of active compound of the desired concentration.

[0889] After the desired period of time, the kill in % is determined.100% means that all aphids have been killed; 0% means that none of theaphids have been killed.

[0890] In this test, for example, the following compounds of thePreparation Examples show good activity: I-2-a-1, I-1-a-5, I-1-a-6 andI-1-a-8.

Example C

[0891] Phaedon Larvae Test Solvent: 30 parts by weight ofdimethylformamide Emulsifier: 1 part by weight of alkylaryl polyglycolether

[0892] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amounts of solventand emulsifier, and the concentrate is diluted withemulsifier-containing water to the desired concentration.

[0893] Cabbage leaves (Brassica oleracea) are treated by being dippedinto the preparation of active compound of the desired concentration andare populated with the larvae of the mustard beetle (Phaedoncochleariae) while the leaves are still moist.

[0894] After the desired period of time, the kill in % is determined.100% means that all beetle larvae have been killed; 0% means that noneof the beetle larvae have been killed.

[0895] In this test, for example, the following compounds of thePreparation Examples show good activity: I-2-a-1, I-2-a-2, I-1-a-3,I-1-a-4, I-1-a-5, I-1-a-6, I-1-a-2, I-1-a-1, I-1-c-1 and I-1-a-8.

Example D

[0896]Spodoptera frugiperda Test Solvent: 30 parts by weight ofdimethylformamide Emulsifier: 1 part by weight of alkylaryl polyglycolether

[0897] To produce a suitable preparation of active compound, I part byweight of active compound is mixed with the stated amounts of solventand emulsifier, and the concentrate is diluted withemulsifier-containing water to the desired concentration.

[0898] Cabbage leaves (Brassica oleracea) are treated by being dippedinto the preparation of active compound of the desired concentration andare populated with caterpillars of the army worm (Spodoptera frugiperda)while the leaves are still moist.

[0899] After the desired period of time, the kill in % is determined.100% means that all caterpillars have been killed; 0% means that none ofthe caterpillars have been killed.

[0900] In this test, for example, the following compounds of thePreparation Examples showed good activity: I-2-a-1, I-1-a-4, I-1-a-5,I-1-a-6, I-1-a-2, I-1-a-1 and I-1-c-1.

Example E

[0901] Tetranychus Test (OP-Resistant/Dip Treatment) Solvent: 30 partsby weight of dimethylformamide Emulsifier: 1 part by weight of alkylarylpolyglycol ether

[0902] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amounts of solventand emulsifier, and the concentrate is diluted withemulsifier-containing water to the desired concentration.

[0903] Bean plants (Phaseolus vulgaris) which are heavily infested byall stages of the greenhouse red spider mite (Tetranychus urticae) aredipped into a preparation of active compound of the desiredconcentration.

[0904] After the desired period of time, the effect in % is determined.100% means that all spider mites have been killed. 0% means that none ofthe spider mites have been killed.

[0905] In this test, for example, the following compounds of thePreparation Examples show good activity: I-2-a-2, I-1-a-4, I-1-a-5 andI-1-a-6.

Example F

[0906] Post-Emergence Test Solvent: 5 parts by weight of acetoneEmulsifier: 1 part by weight of alkylaryl polyglycol ether

[0907] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amount of solvent,the stated amount of emulsifier is added and the concentrate is dilutedwith water to the desired concentration.

[0908] Test plants of a height of 5 to 15 cm are sprayed with thepreparation of active compound such that the particular amounts ofactive compound desired are applied per unit area. The concentration ofthe spray liquor is chosen such that the particular amounts of activecompound desired are applied in 1000 l of water/ha.

[0909] After three weeks, the degree of damage to the plants is rated in% damage in comparison to the development of the untreated control.

[0910] The figures denote:

[0911] 0% =no effect (like untreated control)

[0912] 100% =total destruction

Example G

[0913] Pre-Emergence Test Solvent: 5 parts by weight of acetoneEmulsifier: 1 part by weight of alkylaryl polyglycol ether

[0914] To produce a suitable preparation of active compound, I part byweight of active compound is mixed with the stated amount of solvent,the stated amount of emulsifier is added and the concentrate is dilutedwith water to the desired concentration.

[0915] Seeds of the test plants are sown in normal soil. After about 24hours, the soil is sprayed with the preparation of active compound suchthat the particular amounts of active compound desired are applied perunit area. The concentration of the spray liquor is chosen such that theparticular amounts of active compound desired are applied in 1000 l ofwater/ha.

[0916] After three weeks, the degree of damage to the plants is rated in% damage in comparison to the development of the untreated control.

[0917] The figures denote:

[0918] 0% =no effect (like untreated control)

[0919] 100% =total destruction pre- g sugar oilseed Avena emergenceai/ha beet rape Alopecurus fatua Lolium Setaria Matricaria Ex. I-2-a-1125 0 0 90 100 100 100 100 post- g oilseed Avena Echino- Amaran- Cheno-emergence ai/ha rape Alopecurus Fatua chloa Setaria thus podium Ex.I-2-a-1 250 20 80 95 100 100 70 70 pre- sugar oilseed Avena emergence gai/ha beet rape fatua Bromus Lolium Setaria Ex. I-2-a-2 250 0 0 90 90100 100 Soy post- g sugar a Avena emergence ai/ha beet bean fatuaDigitaria Echinochloa Setaria Ex. I-2-a-2 250 0 0 90 90 100 95 post-emergence g ai/ha Alopecurus Echinochloa Amaranthus Ex. I-1-a-5 250 80100 90 post- emergence g ai/ha sugar beet Alopecurus Avena fatuaDigitaria Echinochloa Ex. I-1-a-6 125 0 90 90 95 90 post- g emergenceai/ha Alopecurus Echinochloa Setaria Amaranthus Ex. I-1-a-2 250 70 90 9590 post- Avena emergence g ai/ha Alopecurus fatua Echinochloa AmaranthusSinapis Ex. I-1-a-1 250 80 80 95 70 80 post- Avena emergence g ai/harice fatua Digitaria Echinochloa Stellaria Ex. I-1-a-3 250 10 100 100100 90 post- Avena emergence g ai/ha Alopecurus fatua EchinochloaSetaria Ex. I-1-c-1 250 80 95 95 90 post- Avena emergence g ai/haAlopecurus fatua Echinochloa Setaria Abutilon Amaranthus Ex.I-1-a-4 25095 100 100 100 80 95 Ex.I-1-b-1 250 95 100 100 100 80 80

Example H

[0920] Critical Concentration Test/Soil Insects—Treatment of TransgenicPlants

[0921] Test insect: Diabrotica balteata—larvae in soil Solvent: 7 partsby weight of acetone Emulsifier: 1 part by weight of alkylarylpolyglycol ether

[0922] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amount of solvent,the stated amount of emulsifier is added and the concentrate is dilutedwith water to the desired concentration.

[0923] The preparation of active compound is poured onto the soil. Here,the concentration of the active compound in the preparation is virtuallyirrelevant, only the amount by weight of active compound per volume unitof soil, which is stated in ppm (mg/l), matters. The soil is filled into0.25 l pots and these are allowed to stand at 20° C.

[0924] Immediately after preparation, 5 pre-germinated maize corns ofthe variety YIELD GUARD (trademark of Monsanto Comp., USA) are placedinto each pot. After 2 days, the test insects concerned are placed intothe treated soil. After a further 7 days, the efficacy of the activecompound is determined by counting the maize plants that have emerged (1plant=20% efficacy).

Example I

[0925]Heliothis virescens Test—Treatment of Transgenic Plants

[0926] Solvent: 7 parts by weight of acetone

[0927] Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0928] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amount of solvent andthe stated amount of emulsifier, and the concentrate is diluted withwater to the desired concentration.

[0929] Soya bean shoots (Glycine max) of the variety Roundup Ready(trademark of Monsanto Comp. USA) are treated by being dipped into thepreparation of active compound of the desired concentration and arepopulated with the tobacco budworm Heliothis virescens while the leavesare still moist.

[0930] After the desired period of time, the kill of the insects isdetermined.

1. Compounds of the formula (I)

in which W represents N—D ⁽¹⁾, oxygen ⁽²⁾ or sulphur ⁽³⁾, Het representsin each case optionally substituted thiazolyl, oxazolyl or pyrazolyl, Arepresents hydrogen, in each case optionally halogen-substituted alkyl,alkenyl, alkoxyalkyl, polyalkoxyalkyl, alkylthioalkyl, saturated orunsaturated optionally substituted cycloalkyl in which optionally atleast one ring atom is replaced by a heteroatom, or in each caseoptionally halogen-, alkyl-, halogenoalkyl, alkoxy-, halogenoalkoxy-,cyano- or nitro-substituted aryl, arylalkyl or hetaryl, B representshydrogen, alkyl or alkoxyalkyl, or A and B together with the carbon atomto which they are attached represent a saturated or unsaturatedunsubstituted or substituted cycle which optionally contains at leastone heteroatom, D represents hydrogen or represents an optionallysubstituted radical from the group consisting of alkyl, alkenyl,alkinyl, alkoxyalkyl, polyalkoxyalkyl, alkylthioalkyl, saturated orunsaturated cycloalkyl in which optionally one or more ring members arereplaced by heteroatoms, arylalkyl, aryl, hetarylalkyl or hetaryl or Aand D together with the atoms to which they are attached represent asaturated or unsaturated cycle which is unsubstituted or substituted inthe A,D moiety and optionally contains at least one heteroatom, Grepresents hydrogen (a) or represents one of the groups

in which E represents a metal ion equivalent or an ammonium ion, Lrepresents oxygen or sulphur, M represents oxygen or sulphur, R¹represents in each case optionally halogen-substituted alkyl, alkenyl,alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl or optionally halogen-,alkyl or alkoxy-substituted cycloalkyl which may be interrupted by atleast one heteroatom, in each case optionally substituted phenyl,phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl, R² represents ineach case optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl,polyalkoxyalkyl or represents in each case optionally substitutedcycloalkyl, phenyl or benzyl, R³ represents alkyl, halogenoalkyl orrepresents in each case optionally substituted phenyl or benzyl, R⁴ andR⁵ independently of one another each represent in each case optionallyhalogen-substituted alkyl, alkoxy, alkylamino, dialkylamino, alkylthio,alkenylthio, cycloalkylthio and represents in each case optionallysubstituted phenyl, benzyl, phenoxy or phenylthio, R⁶ and R⁷independently of one another each represent hydrogen, in each caseoptionally halogen-substituted alkyl, cycloalkyl, alkenyl, alkoxy,alkoxyalkyl, represent optionally substituted phenyl, representoptionally substituted benzyl, or together with the N atom to which theyare attached represent a cycle which is optionally interrupted by oxygenor sulphur.
 2. Compounds of the formula (I) according to claim 1 inwhich Het represents

X represents hydrogen, halogen, C₁-C₆-alkyl, C₁-C₄-halogenoalkyl,C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, nitro or cyano, Y represents halogen,C₁-C₆-alkyl, C₁-C₆-halogenoalkyl, C₁-C₆-alkoxy, C₁-C₆-halogenoalkoxy,C₁-C₆-alkylthio, C₁-C₆-alkylsulphonyl, C₁-C₆-alkylsulphoxinyl orrepresents the group

or in the case of Het=thiazolyl ((I-1-A) to (I-3-A)) also represents

in which V¹ represents hydrogen, halogen, C₁-C₁₂-alkyl, C₁-C₆-alkoxy,C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl,C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, nitro, cyano, phenoxy orrepresents phenyl, phenoxy, phenoxy-C₁-C₄-alkyl, phenyl-C₁-C₄-alkoxy,phenylthio-C₁-C₄-alkyl or phenyl-C₁-C₄-alkylthio, each of which isoptionally mono- or polysubstituted by halogen, C₁-C₆-alkyl,C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, nitro or cyano,V² and V³ independently of one another each represent hydrogen, halogen,C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl or C₁-C₄-halogenoalkoxy,V¹ and V² together with the carbon atoms to which they are attachedrepresent an optionally C₁-C₄-alkyl- or halogen-substituted saturated orunsaturated 5- or 6-membered cycle in which optionally one to threecarbon atoms may be replaced by oxygen, sulphur or nitrogen, Wrepresents N—D⁽¹⁾, oxygen⁽²⁾ or sulphur⁽³⁾, A represents hydrogen or ineach case optionally fluorine- or chlorine-substituted C₁-C₁₂-alkyl,C₃-C₈-alkenyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, poly-C₁-C₆-alkoxy-C₁-C₆-alkyl,C₁-C₁₀-alkylthio-C₁-C₆-alkyl, optionally fluorine-, chlorine-,C₁-C₆-alkyl- or C₁-C₆-alkoxy-substituted C₃-C₈-cycloalkyl in whichoptionally one or two not directly adjacent ring members are replaced byoxygen and/or sulphur or represents in each case optionally halogen-,C₁-C₆-alkyl-, C₁-C₆-halogenoalkyl-, C₁-C₆-alkoxy-,C₁-C₆-halogenoalkoxy-, cyano- or nitro-substituted C₆- or C₁₀-aryl.hetaryl having 5 or 6 ring atoms or C₆- or C₁₀-aryl-C₁-C₆-alkyl, Brepresents hydrogen, C₁-C₆-alkyl or C₁-C₄-alkoxy-C₁-C₄-alkyl, or A, Band the carbon atom to which they are attached represent saturatedC₃-C₁₀-cycloalkyl or unsaturated C₅-C₁₀-cycloalkyl in which optionallyone ring member is replaced by oxygen or sulphur and which areoptionally mono- or disubstituted by C₁-C₆-alkyl, C₃-C₈-cycloalkyl,C₁-C₄-halogenoalkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio, halogen or phenyl orA, B and the carbon atom to which they are attached representC₅-C₆-cycloalkyl which is substituted by an alkylenediyl group whichoptionally contains an oxygen or sulphur atom, or by an alkylenedioxylor by an alkylenedithioyl group which, together with the carbon atom towhich it is attached, forms a further five- or six-membered ring whichmay optionally be mono- to tetrasubstituted by C₁-C₄-alkyl, or A, B andthe carbon atom to which they are attached represent C₃-C₈-cycloalkyl orC₅-C₈-cycloalkenyl in which two substituents together with the carbonatoms to which they are attached represent in each case optionallyC₁-C₆-alkyl-, C₁-C₆-alkoxy- or halogen-substituted C₂-C₆-alkanediyl,C₂-C₆-alkenediyl or C₄-C₆-alkanedienediyl in which optionally onemethylene group is replaced by oxygen or sulphur, D represents hydrogen,in each case optionally halogen- or cyano-substituted C₁-C₁₂-alkyl,C₃-C₈-alkenyl, C₃-C₈-alkinyl, C₁-C₁₀-alkoxy-C₂-C₈-alkyl,poly-C₁-C₈-alkoxy-C₂-C₈-alkyl, C₁-C₁₀-alkylthio-C₂-C₈-alkyl, optionallyhalogen-, C₁-C₄-alkyl-, C₁-C₄-alkoxy- or C₁-C₄-halogenoalkyl-substitutedC₃-C₈-cycloalkyl in which optionally one ring member is replaced byoxygen or sulphur or in each case optionally halogen-, C₁-C₆-alkyl-,C₁-C₆-halogenoalkyl, C₁-C₆-alkoxy-, C₁-C₆-halogenoalkoxy-, cyano- ornitro-substituted phenyl, hetaryl having 5 or 6 ring atoms,phenyl-C₁-C₆-alkyl or hetaryl-C₁-C₆-alkyl having 5 or 6 ring atoms, or Aand D together represent in each case optionally substitutedC₃-C₆-alkanediyl or C₃-C₆-alkenediyl in which optionally one methylenegroup is replaced by a carbonyl group, oxygen or sulphur, possiblesubstituents being in each case: halogen, hydroxyl, mercapto or in eachcase optionally halogen-substituted C₁-C₁₀-alkyl, C₁-C₆-alkoxy,C₁-C₆-alkylthio, C₃-C₇-cycloalkyl, phenyl or benzyloxy, or a furtherC₃-C₆-alkanediyl grouping, C₃-C₆-alkenediyl grouping or a butadienylgrouping which is optionally substituted by C₁-C₆-alkyl or in whichoptionally two adjacent substituents together with the carbon atoms towhich they are attached form a further saturated or unsaturated cyclehaving 5 or 6 ring atoms (in the case of the compound of the formula(I-1-A) to (I-1-B), A and D together with the atoms to which they areattached in this case represent, for example, the groups AD-1 to AD-10mentioned further below) which may contain oxygen or sulphur, or whichoptionally contains one of the groups below

G represents hydrogen (a) or represents one of the groups

in which E represents a metal ion equivalent or an ammonium ion, Lrepresents oxygen or sulphur and M represents oxygen or sulphur, R¹represents in each case optionally halogen-substituted C₁-C₂₀-alkyl,C₂-C₂₀-alkenyl, C₁-C₈-alkoxy-C₁-C₈-alkyl, C₁-C₈-alkylthio-C₁-C₈-alkyl,poly-C₁-C₈-alkoxy-C₁-C₈-alkyl or optionally halogen-, C₁-C₆-alkyl- orC₁-C₆-alkoxy-substituted C₃-C₈-cycloalkyl in which optionally one ormore not directly adjacent ring members are replaced by oxygen and/orsulphur, represents optionally halogen-, cyano-, nitro-, C₁-C₆-alkyl,C₁-C₆-alkoxy-, C₁-C₆-halogenoalkyl-, C₁-C₆-halogenoalkoxy-,C₁-C₆-alkylthio- or C₁-C₆-alkylsulphonyl-substituted phenyl, representsoptionally halogen-, nitro-, cyano-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-,C₁-C₆-halogenoalkyl- or C₁-C₆-halogenoalkoxy-substitutedphenyl-C₁-C₆-alkyl, represents optionally halogen-, C₁-C₆-alkyl-,C₁-C₂-halogenoalkyl- or C₁-C₄-alkoxy-substituted 5- or 6-memberedhetaryl, represents optionally halogen- or C₁-C₆-alkyl-substitutedphenoxy-C₁-C₆-alkyl or represents optionally halogen-, amino- orC₁-C₆-alkyl-substituted 5- or 6-membered hetaryloxy-C₁-C₆-alkyl, R²represents in each case optionally halogen-substituted C₁-C₂₀-alkyl,C₂-C₂₀-alkenyl, C₁-C₈-alkoxy-C₂-C₈-alkyl, poly-C₁-C₈-alkoxy-C₂-C₈-alkyl,represents optionally halogen-, C₁-C₆-alkyl or C₁-C₆-alkoxy-substitutedC₃-C₈-cycloalkyl in which optionally one ring atom is replaced byoxygen, or represents in each case optionally halogen-, cyano-, nitro-,C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₆-halogenoalkyl- orC₁-C₆-halogenoalkoxy-substituted phenyl or benzyl, R³ representsoptionally halogen-substituted C₁-C₈-alkyl or represents in each caseoptionally halogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₄-halogenoalkyl-,C₁-C₄-halogenoalkoxy-, cyano- or nitro-substituted phenyl or benzyl, R⁴and R⁵ independently of one another each represent in each caseoptionally halogen-substituted C₁-C₈-alkyl, C₁-C₈-alkoxy,C₁-C₈-alkylamino, di-(C₁-C₈-alkyl)amino, C₁-C₈-alkylthio,C₂-C₈-alkenylthio, C₃-C₇-cycloalkylthio or represent in each caseoptionally halogen-, nitro-, cyano-, C₁-C₄-Alkoxy-,C₁-C₄-halogenoalkoxy-, C₁-C₄-alkylthio-, C₁-C₄-halogenoalkylthio-,C₁-C₄-alkyl- or C₁-C₄-halooenoalkyl-substituted phenyl, phenoxy orphenylthio, R⁶ and R⁷ independently of one another each representhydrogen, represent in each case optionally halogen-substitutedC₁-C₈-alkyl, C₃-C₈-cycloalkyl, C₁-C₈-alkoxy, C₃-C₈-alkenyl,C₁-C₈-alkoxy-C₁-C₈-alkyl, represent optionally halogen-,C₁-C₈-halogenoalkyl-, C₁-C₈-alkyl- or C₁ -C₈-alkoxy-substituted phenyl,optionally halogen-, C₁-C₈-alkyl-, C₁-C₈-halogenoalkyl- orC₁-C₈-alkoxy-substituted benzyl or together represent an optionallyC₁-C₄-alkyl-substituted C₃-C₆-alkylene radical in which optionally onecarbon atom is replaced by oxygen or sulphur, R¹³ represents hydrogen,represents in each case optionally halogen-substituted C₁-C₈-alkyl orC₁-C₈-alkoxy, represents optionally halogen-, C₁-C₄-alkyl- orC₁-C₄-alkoxy-substituted C₃-C₈-cycloalkyl, in which optionally onemethylene group is replaced by oxygen or sulphur, or represents in eachcase optionally halogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-,C₁-C₄-halogenoalkyl-, C₁-C₄-halogenoalkoxy-, nitro- or cyano-substitutedphenyl, phenyl-C₁-C₄-alkyl or phenyl-C₁-C₄-alkoxy, R¹⁴ representshydrogen or C₁-C₈-alkyl or R¹³ and R¹⁴ together representC₄-C₆-alkanediyl, R¹⁵ and R¹⁶ are identical or different and eachrepresent C₁-C₆-alkyl or R¹⁵ and R¹⁶ together represent aC₂-C₄-alkanediyl radical which is optionally substituted by C₁-C₆-alkyl,C₁-C₆-halogenoalkyl or by optionally halogen-, C₁-C₆-alkyl-,C₁-C₄-halogenoalkyl-, C₁-C₆-alkoxy-, C₁-C₄-halogenoalkoxy-, nitro- orcyano-substituted phenyl, R¹⁷ and R¹⁸ independently of one another eachrepresent hydrogen, represent optionally halogen-substituted C₁-C₈-alkylor represent optionally halogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-,C₁-C₄-halogenoalkyl-, C₁-C₄-halogenoalkoxy-, nitro- or cyano-substitutedphenyl or R¹⁷ and R¹⁸ together with the carbon atom to which they areattached represent a carbonyl group or represent optionally halogen-,C₁-C₄-alkyl or C₁-C₄-alkoxy-substituted C₅-C₇-cycloalkyl in whichoptionally one methylene group is replaced by oxygen or sulphur, R¹⁹ andR²⁰ independently of one another each represent C₁-C₁₀-alkyl,C₂-C₁₀-alkenyl, C₁-C₁₀-alkoxy, C₁-C₁₀-alkylamino, C₃-C₁₀-alkenylamino,di-(C₁-C₁₀-alkyl)amino or di-(C₃-C₁₀-alkenyl)amino.
 3. Compounds of theformula (I) according to claim 1 in which Het represents

X represents hydrogen, chlorine, bromine, C₁-C₄-alkyl,C₁-C₂-halogenoalkyl, nitro or cyano, Y represents chlorine, bromine,C₁-C₄-alkyl, C₁-C₄-halogenoalkyl, C₁-C₄-alkoxy, C₁-C₄-halogenoalkoxy,C₁-C₄-alkylthio, C₁ -C₄-alkylsulphonyl or represents the group

or in the case of Het=thiazolyl ((I-1-A) to (1-3-A)) also represents

in which V¹ represents hydrogen, fluorine, chlorine, bromine,C₁-C₆-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl, C₁-C₂-halogenoalkoxy,nitro, cyano, phenoxy or represents phenyl, phenoxy,phenoxy-C₁-C₂-alkyl, phenyl-C₁-C₂-alkoxy, phenylthio-C₁-C₂-alkyl orphenyl-C₁-C₂-alkylthio, each of which is optionally mono- ordisubstituted by fluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy,C₁-C₂-halogenoalkyl, C₁-C₂-halogenoalkoxy, nitro or cyano, V² representshydrogen, fluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy,C₁-C₂-halogenoalkyl or C₁-C₂-halogenoalkoxy, or V¹ and V² together withthe carbon atoms to which they are attached represent an optionallyfluorine- or methyl-substituted 5- or 6-membered cycle in whichoptionally one or two carbon atoms may be replaced by oxygen, Wrepresents N—D⁽¹⁾, oxygen⁽²⁾ or sulphur⁽³⁾, A represents hydrogen, ineach case optionally fluorine-substituted C₁-C₁₀-alkyl,C₁-C₄-alkoxy-C₁-C₄-alkyl, optionally fluorine-, chlorine-, C₁-C₄-alkyl-or C₁-C₄-alkoxy-substituted C₃-C₇-cycloalkyl in which optionally onering member is replaced by oxygen or sulphur or in each case optionallyfluorine-, chlorine-, bromine-, C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-,C₁-C₄-alkoxy- or C₁-C₄-halogenoalkoxy-substituted phenyl orphenyl-C₁-C₂-alkyl, B represents hydrogen or C₁-C₄-alkyl, or A, B andthe carbon atom to which they are attached represent saturatedC₅-C₇-cycloalkyl in which optionally one ring member is replaced byoxygen or sulphur and which is optionally mono- or disubstituted byC₁-C₆-alkyl, C₅-C₆-cycloalkyl, C₁-C₂-halogenoalkyl, C₁-C₆-alkoxy,fluorine, chlorine or phenyl or A, B and the carbon atom to which theyare attached represent C₅-C₆-cycloalkyl which is substituted by analkylenediyl group which optionally contains an oxygen or sulphur atomor by an alkylenedioxyl or by an alkylenedithioyl group which togetherwith the carbon atom to which it is attached forms a further five- orsix-membered ring which may optionally be mono- to trisubstituted byC₁-C₃-alkyl, or A, B and the carbon atom to which they are attachedrepresent C₅-C₆-cycloalkyl or C₅-C₆-cycloalkenyl in which twosubstituents together with the carbon atoms to which they are attachedrepresent in each case optionally C₁-C₅-alkyl-, C₁-C₅-alkoxy-,fluorine-, chlorine- or bromine-substituted C₂-C₄-alkanediyl,C₂-C₄-alkenediyl in which optionally one methylene group is replaced byoxygen or sulphur or represent butadienediyl, D represents hydrogen,represents in each case optionally fluorine-substituted C₁-C₁₀-alkyl,C₃-C₆-alkenyl, C₁-C₆-alkoxy-C₂-C₄-alkyl or C₁-C₆-alkylthio-C₂-C₄-alkyl,represents optionally fluorine-C₁-C₄-alkyl, C₁-C₄-alkoxy orC₁-C₂-halogenoalkyl-substituted C₃-C₇-cycloalkyl, in which optionallyone methylene group is replaced by oxygen or sulphur or represents ineach case optionally fluorine-, chlorine-, bromine-, C₁-C₄-alkyl-,C₁-C₂-halogenoalkyl-, C₁-C₄-alkoxy- or C₁-C₂-halogenoalkoxy-substitutedphenyl or phenyl-C₁-C₄-alkyl, or A and D together represent optionallysubstituted C₃-C₅-alkanediyl in which optionally one methylene group maybe replaced by a carbonyl group, oxygen or sulphur, possiblesubstituents being hydroxyl, C₁-C₆-alkyl or C₁-C₄-alkoxy, or A and Dtogether with the atoms to which they are attached represent one of thegroups AD-1 to AD-10:

G represents hydrogen (a) or represents one of the groups

in which E represents a metal ion equivalent or an ammonium ion, Lrepresents oxygen or sulphur and M represents oxygen or sulphur, R¹represents in each case optionally fluorine- or chlorine-substitutedC₁-C₁₆-alkyl, C₂-C₁₆-alkenyl, C₁-C₆-alkoxy-C₁-C₄-alkyl,C₁-C₆-alkylthio-C₁-C₄-alkyl or optionally fluorine-, chlorine-,C₁-C₅-alkyl- or C₁-C₅-alkoxy-substituted C₃-C₇-cycloalkyl in whichoptionally one or two not directly adjacent ring members are replaced byoxygen and/or sulphur, represents optionally fluorine-, chlorine-,bromine-, cyano-, nitro-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-,C₁-C₃-halogenoalkyl-, C₁-C₃-halogenoalkoxy-, C₁-C₄-alkylthio- orC₁-C₄-alkylsulphonyl-substituted phenyl, represents optionallyfluorine-, chlorine-, bromine-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-,C₁-C₃-halogenoalkyl- or C₁-C₃-halogenoalkoxy-substitutedphenyl-C₁-C₄-alkyl, represents in each case optionally fluorine-,chlorine-, bromine-, C₁-C₄-alkyl-, trifluoromethyl- orC₁-C₂-alkoxy-substituted pyrazolyl, thiazolyl, pyridyl, pyrimidyl,furanyl or thienyl, R² represents in each case optionallyfluorine-substituted C₁-C₁₆-alkyl, C₂-C₁₆-alkenyl orC₁-C₆-alkoxy-C₂-C₆-alkyl, represents optionally fluorine-, chlorine-,C₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted C₃-C₇-cycloalkyl or representsin each case optionally fluorine-, chlorine-, bromine-, cyano-, nitro-,C₁-C₄-alkyl-, C₁-C₃-alkoxy-, C₁-C₂-halogenoalkyl- orC₁-C₂-halogenoalkoxy-substituted phenyl or benzyl, R³ representsoptionally fluorine-substituted C₁-C₆-alkyl or represents optionallyfluorine-, chlorine-, bromine-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-,C₁-C₃-halogenoalkyl-, C₁-C₃-halogenoalkoxy-, cyano- or nitro-substitutedphenyl, R⁴ represents C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylamino,di-(C₁-C₆-alkyl)amino, C₁-C₆-alkylthio, C₃-C₄-alkenylthio,C₃-C₆-cycloalkylthio or represents in each case optionally fluorine-,chlorine-, bromine-, nitro-, cyano-, C₁-C₃-alkoxy-,C₁-C₃-halogenoalkoxy-, C₁-C₃-alkylthio-, C₁-C₃-halogenoalkylthio-,C₁-C₃-alkyl- or C₁-C₃-halogenoalkyl-substituted phenyl, phenoxy orphenylthio, R⁵ represents C₁-C₆-alkoxy or C₁-C₆-alkylthio, R⁶ representsC₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₃-C₆-alkenyl,C₁-C₆-alkoxy-C₁-C₆-alkyl, represents optionally fluorine-, chlorine-,bromine-, C₁-C₃-halogenoalkyl-, C₁-C₄-alkyl- or C₁-C₄-alkoxy-substitutedphenyl, represents optionally fluorine-, chlorine-, bromine-,C₁-C₄-alkyl-, C₁-C₃-halogenoalkyl- or C₁-C₄-alkoxy-substituted benzyl,R⁷ represents hydrogen, C₁-C₆-alkyl, C₃-C₆-alkenyl, or R⁶ and R⁷together represent an optionally methyl- or ethyl-substitutedC₄-C₅-alkylene radical in which optionally one methylene group isreplaced by oxygen or sulphur.
 4. Compounds of the formula (I) accordingto claim I in which Het represents

X represents hydrogen, chlorine, bromine, methyl, ethyl, n-propyl,iso-propyl, n-butyl or iso-butyl, Y represents methyl, ethyl, n-propyl,i-propyl, n-butyl, i-butyl, tert-butyl, trifluoromethyl or representsthe group

or in the case of Het=thiazolyl ((I-1-A) to (I-3-A)) also represents

in which V¹ represents hydrogen, fluorine, chlorine, bromine, methyl,ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, tert-butyl, methoxy,ethoxy, n-propoxy, iso-propoxy, trifluoromethyl, trifluoromethoxy,nitro, cyano, phenoxy or phenyl which is optionally mono- ordisubstituted by fluorine, chlorine, methyl, methoxy, trifluoromethyl ortrifluoromethoxy, V² represents hydrogen, fluorine, chlorine, methyl,ethyl, n-propyl, iso-propyl, methoxy, ethoxy, trifluoromethyl ortrifluoromethoxy, or V¹ and V² together represent —O—CH₂—O—, —O—CF₂—O—or —O—CF₂—CF₂—O—, W represents N—D⁽¹⁾, oxygen⁽²⁾ or sulphur⁽³⁾, Arepresents hydrogen, represents in each case optionallyfluorine-substituted C₁-C₈-alkyl or C₁-C₄-alkoxy-C₁-C₂-alkyl, optionallyfluorine-, methyl-, ethyl- or methoxy-substituted C₃-C₆-cycloalkyl inwhich optionally one ring member is replaced by oxygen or sulphur orrepresents in each case optionally fluorine-, chlorine-, bromine-,methyl-, ethyl-, n-propyl-, iso-propyl-, tert-butyl-, methoxy-, ethoxy-,trifluoromethyl-, trifluoromethoxy-, cyano- or nitro-substituted phenylor benzyl, B represents hydrogen, methyl or ethyl, or A, B and thecarbon atom to which they are attached represent saturatedC₅-C₆-cycloalkyl in which optionally one ring member is replaced byoxygen or sulphur and which is optionally mono- or disubstituted bymethyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl,tert-butyl, trifluoromethyl, methoxy, ethoxy, propoxy, iso-propoxy,butoxy or iso-butoxy or A, B and the carbon atom to which they areattached represent C₆-cycloalkyl which is substituted by analkylenedioxyl group which is optionally mono- or disubstituted bymethyl or ethyl and which together with the carbon atom to which it isattached forms a further five- or six-membered ring or A, B and thecarbon atom to which they are attached represent C₅-C₆-cycloalkyl orC₅-C₆-cycloalkenyl in which two substituents together with the carbonatoms to which they are attached represent C₂-C₄-alkanediyl orC₂-C₄-alkenediyl in which in each case optionally one methylene group isreplaced by oxygen or sulphur, or represent butadienediyl, D representshydrogen, represents in each case optionally fluorine-substitutedC₁-C₆-alkyl, C₃-C₄-alkenyl, C₁-C₄-alkoxy-C₂-C₃-alkyl,C₁-C₄-alkylthio-C₂-C₃-alkyl or C₃-C₆-cycloalkyl in which optionally onemethylene group is replaced by oxygen or sulphur or represents in eachcase optionally fluorine-, chlorine-, methyl-, ethyl-, n-propyl-,iso-propyl-, methoxy-, ethoxy-, trifluoromethyl- ortrifluoromethoxy-substituted phenyl or benzyl, or A and D togetherrepresent optionally substituted C₃-C₄-alkanediyl in which optionallyone carbon atom is replaced by oxygen or sulphur and which is optionallysubstituted by methyl or A and D (in the case of the compounds of theformula (I-1)) together with the atoms to which they are attachedrepresent one of the groups AD below:

G represents hydrogen (a) or represents one of the groups

in which E represents a metal ion equivalent or an ammonium ion, Lrepresents oxygen or sulphur and M represents oxygen or sulphur, R¹represents in each case optionally fluorine-substituted C₁-C₄-alkyl,C₂-C₁₄-alkenyl, C₁-C₄-alkoxy-C₁-C₂-alkyl, C₁-C₄-alkylthio-C₁-C₂-alkyl orin each case optionally fluorine-, chlorine-, methyl-, ethyl- ormethoxy-substituted cyclopropyl, cyclopentyl or cyclohexyl, representsphenyl which is optionally mono- or disubstituted by fluorine, chlorine,bromine, cyano, nitro, methyl, ethyl, tert-butyl, methoxy, ethoxy,trifluoromethyl or trifluoromethoxy, represents thienyl or pyridyl, eachof which is optionally monosubstituted by fluorine, chlorine, bromine ormethyl, R² represents in each case optionally fluorine-substitutedC₁-C₈-alkyl, C₂-C₈-alkenyl or C₁-C₄-alkoxy-C₂-C₃-alkyl, representsoptionally fluorine-, chlorine-, methyl-, ethyl-, n-propyl-, iso-propyl-or methoxy-substituted cyclohexyl, or represents in each case optionallyfluorine-, chlorine-, cyano-, nitro-, methyl-, ethyl-, methoxy-,trifluoromethyl- or trifluoromethoxy-substituted phenyl or benzyl, R³represents methyl, ethyl, n-propyl or represents phenyl which isoptionally monosubstituted by fluorine, chlorine, bromine, methyl,tert-butyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro,R⁴ represents C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylamino,di-(C₁-C₄-alkyl)amino, C₁-C₄-alkylthio or represents in each caseoptionally fluorine-, chlorine-, bromine-, nitro-, cyano-,C₁-C₂-alkoxy-, C₁-C₂-fluoroalkoxy-, C₁-C₂-alkylthio-,C₁-C₂-fluoroalkylthio- or C₁-C₃-alkyl-substituted phenyl, phenoxy orphenylthio, R⁵ represents methoxy, ethoxy, methylthio or ethylthio, R⁶represents C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-alkoxy, C₃-C₄-alkenyl,C₁-C₄-alkoxy-C₁-C₄-alkyl, represents optionally fluorine-, chlorine-,bromine-, trifluoromethyl-, methyl- or methoxy-substituted phenyl,represents optionally fluorine-, chlorine-, bromine-, methyl-,trifluoromethyl- or methoxy-substituted benzyl, R⁷ represents hydrogen,methyl, ethyl, propyl or allyl, or R⁶ and R⁷ together represent aC₅-C₆-alkylene radical in which optionally one methylene group isreplaced by oxygen or sulphur.
 5. Compounds of the formula (I) accordingto claim 1 in which Het represents

X represents hydrogen, chlorine, bromine, methyl, ethyl, n-propyl, oriso-propyl, Y represents methyl, ethyl, n-propyl, i-propyl, n-butyl,i-butyl, tert-butyl, trifluoromethyl or represents the group

or in the case of Het=thiazolyl ((I-1-A) or (I-3-A)) also represents

in which V¹ represents hydrogen, fluorine, chlorine, bromine, methyl,ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, tert-butyl, methoxy,ethoxy, n-propoxy, iso-propoxy, trifluoromethyl, trifluoromethoxy,phenoxy, represents optionally chlorine- or trifluoromethyl-substitutedphenyl, V² represents hydrogen, fluorine, chlorine, methyl, ethyl,methoxy or trifluoromethyl, or V¹ and V² together represent —O—CH—O— or—O—CF₂—O—, W represents N—D⁽¹⁾, oxygen⁽²⁾ or sulphur⁽³⁾, A representshydrogen or C₁-C₄-alkyl or cyclopropyl, B represents hydrogen or methyl,or A, B and the carbon atom to which they are attached representsaturated C₅-C₆-cycloalkyl in which optionally one ring member isreplaced by oxygen or sulphur, and which is optionally mono- ordisubstituted by methyl, ethyl, propyl, isopropyl, trifluoromethyl,methoxy, ethoxy, propoxy, butoxy or iso-butoxy, or representsC₅-C₆-cycloalkyl in which two not directly adjacent carbon atoms form afurther five-membered ring, D represents hydrogen, D also representsi-propyl, A and D together with the atoms to which they are attachedrepresent cyclohexyl in which one ring atom may be replaced by sulphur,G represents hydrogen (a) or in the case of Het=thiazolyl ((I-1-A) to(I-3-A)) represents one of the groups

in which L represents oxygen and M represents oxygen, R¹ represents ineach case optionally fluorine- or chlorine-substituted C₁-C₄-alkyl,C₂-C₄-alkenyl, C₁-C₄-alkoxy-C₁-C₂-alkyl, C₁-C₄-alkylthio-C₁-C₂-alkyl oroptionally fluorine-, chlorine-, methyl-, ethyl- or methoxy-substitutedcyclopropyl or cyclohexyl, represents phenyl which is optionallymonosubstituted by fluorine, chlorine, bromine, cyano, nitro, methyl,ethyl, n-propyl, i-propyl, tert-butyl, methoxy, ethoxy, i-propoxy,tert-butoxy, trifluoromethyl or trifluoromethoxy, represents thienyl orpyridyl, each of which is optionally monosubstituted by chlorine ormethyl, R² represents optionally in each case fluorine-substitutedC₁-C₄-alkyl, C₂-C₄-alkenyl or C₁-C₄-alkoxy-C₂-C₃-alkyl, representsoptionally methyl-, ethyl-, n-propyl-, iso-propyl- ormethoxy-substituted cyclohexyl, or represents phenyl or benzyl, each ofwhich is optionally monosubstituted by fluorine, chlorine, cyano, nitro,methyl, ethyl, methoxy, trifluoromethyl or trifluoromethoxy. 6.Compounds of the formula (I) according to claim 1 in which Hetrepresents

X represents methyl, ethyl, n-propyl, i-propyl, chlorine or bromine, Yrepresents methyl, ethyl, n-propyl or i-propyl or represents the groups

in which V¹ represents hydrogen, bromine, chlorine, methyl,trifluoromethyl, phenoxy or t-butyl or represents optionally chlorine-or trifluoromethyl-substituted phenyl, V² represents hydrogen, chlorine,fluorine or methoxy or V¹ and V² together represent —O—CH₂—O— or—O—CF₂—O—, W represents N—D⁽¹⁾, oxygen⁽²⁾ or sulphur⁽³⁾, D representshydrogen or i-propyl, A represents methyl, ethyl, n- or i-propyl orcyclopropyl or hydrogen, B represents hydrogen or methyl, or A and B andthe carbon atom to which they are attached represent cyclohexyl in whichoptionally one ring atom is replaced by oxygen and which is optionallymono- or disubstituted by methyl, ethyl, methoxy or ethoxy, or representcyclohexyl in which two not directly adjacent carbon atoms form afurther 5-membered C ring, A and D together with the atoms to which theyare attached represent cyclohexyl in which one ring atom may be replacedby sulphur, G represents hydrogen (a) or represents one of the groups

in which R¹ represents methyl, ethyl, n-propyl or i-propyl or representsin each case optionally chlorine-substituted phenyl or pyridyl, R²represents methyl, ethyl, phenyl, benzyl, n- or i-propyl.
 7. Compoundsof the formula (I) according to claim 1 in which Het represents

X represents methyl or ethyl, Y represents optionallychlorine-substituted phenyl, A represents methyl, ethyl, n- or i-propyl,B represents methyl, or A and B and the carbon atom to which they areattached together represent cyclohexyl which is optionally substitutedby methoxy or methyl W represents N—D or oxygen, D represents hydrogen,G represents hydrogen.
 8. Process for preparing compounds of the formula(I) according to claim 1, characterized in that (A) compounds of theformulae (I-1-A-a) to (I-1-Ba)

(I-1-A-a) to (I-1-B-a) in which A, B, D and Het are each as definedabove are obtained when compounds of the formula (II)

in which A, B, D and Het are each as defined above and R⁸ representsalkyl are condensed intramolecularly in the presence of a diluent and inthe presence of a base, (B) compounds of the formulae (I-2-A-a) to(I-2-B-a)

(I-2-A-a) to (I-2-B-a) in which A, B and Het are each as defined aboveare obtained when compounds of the formula (III)

in which A, B, Het and R⁸ are each as defined above are condensedintramolecularly in the presence of a diluent and in the presence of abase, (C) compounds of the formulae (I-3-A-a) to (I-3-B-a)

(I-3-A-a) to (I-3-B-a) in which A, B and Het are each as defined above,are obtained when compounds of the formula (IV)

in which A, B, Het and R⁸ are each as defined above and W¹ representshydrogen, halogen, alkyl or alkoxy, are cyclized intramolecularly, ifappropriate in the presence of a diluent and in the presence of an acid,and, if appropriate, the resulting compounds of the formulae (I-1-A-a)to (I-3-B-a), in which A, B, D and Het are each as defined above are ineach case reacted (D) (α) with acyl halides of the formula (V)

in which R¹ is as defined above and Hal represents halogen or (β) withcarboxylic anhydrides of the formula (VI) R¹—CO—O—CO—R¹  (VI) in whichR¹ is as defined above, if appropriate in the presence of a diluent andif appropriate in the presence of an acid binder; (E) with chloroformicesters or chloroformic thioesters of the formula (VII) R²—M—CO—Cl  (VII)in which R² and M are each as defined above, if appropriate in thepresence of a diluent and if appropriate in the presence of an acidbinder; (F) with chloromonothioformic esters or chlorodithioformicesters of the formula (VEII)

in which M and R² are each as defined above, if appropriate in thepresence of a diluent and if appropriate in the presence of an acidbinder and (G) with sulphonyl chlorides of the formula (IX)R³—SO₂—Cl  (IX) in which R³ is as defined above, if appropriate in thepresence of a diluent and if appropriate in the presence of an acidbinder, (H) with phosphorus compounds of the formula (X)

in which L, R⁴ and R⁵ are each as defined above and Hal representshalogen, if appropriate in the presence of a diluent and if appropriatein the presence of an acid binder, (I) with metal compounds or amines ofthe formula (XI) or (XII) Me(OR¹⁰)_(t)  (XI)

in which Me represents a mono- or divalent metal, t represents thenumber 1 or 2 and R¹⁰, R¹¹, R¹² independently of one another eachrepresent hydrogen or alkyl, if appropriate in the presence of adiluent, (J) (α) with isocyanates or isothiocyanates of the formula(XIII) R⁶—N═C═L  (XIII) in which R⁶ and L are each as defined above, ifappropriate in the presence of a diluent and if appropriate in thepresence of a catalyst, or (β) with carbamoyl chlorides or thiocarbamoylchlorides of the formula (XIV)

in which L, R⁶ and R⁷ are each as defined above, if appropriate in thepresence of a diluent and if appropriate in the presence of an acidbinder.
 9. Compounds of the formula (II)

in which A, B, D, Het and R⁸ are each as defined above.
 10. Compounds ofthe formula (XVII)

in which A, B, D and Het are each as defined above.
 11. Compounds of theformula (XXI)

in which A, B, D and Het are each as defined above.
 12. Compounds of theformula (III)

in which A, B, Het and R⁸ are each as defined above.
 13. Compounds ofthe formula (IV)

in which A, B, W¹, Het and R⁸ are each as defined above and W¹represents hydrogen, halogen, alkyl or alkoxy.
 14. Pesticides andherbicides, characterized in that they comprise at least one compound ofthe formula (I) according to claim
 1. 15. Use of compounds of theformula (I) according to claim 1 for controlling pests and weeds. 16.Method for controlling pests and weeds, characterized in that compoundsof the formula (I) according to claim 1 are allowed to act on pestsand/or their habitat or on weeds and/or their habitat.
 17. Process forpreparing pesticides and herbicides, characterized in that compounds ofthe formula (I) according to claim 1 are mixed with extenders and/orsurfactants.
 18. Use of compounds of the formula (I) according to claim1 for preparing pesticides and herbicides.